Strictly Business
by LoganHendersonLVR2003
Summary: James Diamond is the heir to Diamond Cosmetics, a multi-million dollar company that is based in every major city in the United States. James is a bachelor, a stud, and an excellent negotiator, he could have anybody he wants, any time he wants them. So why does he find himself so enamored with a random scruffy blonde who's selling his body on an adult webcam site? GRAPHIC KAMES
1. Tall, Blonde, and Eyebrows

_**Monday Morning, New York**_

* * *

"Kelly, I'm gonna need you to reschedule that conference I have tomorrow at ten. I have two contracts I need to get signed up with Dak Zevon and his management, and then we're gonna have to negotiate a deal with him. And be sure that my team knows that the board meeting is back on again for Thursday. Also, have you heard from Gustavo yet? That bastard still isn't budging, and I need to get in contact with him as soon as possible.", the sharply dressed man said, his hand rubbing his stubble as he planned out what was on the agenda for the following day.

Adjusting the cuffs on his dress shirt, James was currently gazing out the window of his 47th floor office, prime estate in a business capital like New York City. Turning back, he walked towards his desk, quickly answering the call that his assistant, Kelly, had put on hold for him. It was something miniscule, something James just didn't have the time for, so he hung up and began muttering to himself about people bothering him for the stupidest of reasons.

The dark-skinned woman quickly jotted down notes, taking into account as to what she would need to quickly finish before the day was over. She was used to James giving her _many_ , _**many**_ tasks, things which would make any other person break down from the levels of stress. But not her, though. Kelly was amazing at her job, she was a powerhouse who could get things done before you were finished telling her about them, and what seemed like a workload for others was nothing more than a quick assignment for her.

Both brains and beauty, she was the best at what she did, and James loved her for it. Kelly was a speed demon, a worker who could truly handle the fast paced environment James Diamond set upon them. The two worked very well together, both actually very close friends with the greatest amount of respect for one another. A day didn't go by where James didn't thank the gods for gracing him in the presence of Kelly Wainwright.

Outside of work, the two didn't spend too much time with one another, mostly due to them having such busy lives. With what time they could squeeze in together that didn't focus on whatever negotiation that needed to be made, the two would try to grab lunch together, or anything of the sort. Having only been working together for the past year, the two really hit it off, James seeing her as the sister he always wanted, and her likewise.

After what had happened the previous year, James was glad that fate was still on his side.

James Diamond, the 34-year old bachelor with a body to kill for and a smile that could charm just about anybody, was one of the most prolific young entrepreneurs in all of New York. Having inherited the family business, Diamond Cosmetics, from his mother, the late Brooke Diamond, James just had a natural sense of business savvy, prevalent throughout his life. He was a natural born leader, not only book smart but also charismatic, he was the package deal. While he wasn't actually in charge of anybody, instead working with a team of some of his mother's most trusted business associates, he was quickly on his way to a promotion, something those who had been working decades could only dream of.

It's also what landed him in the nasty situation he wished he could have just forgotten.

Originally stationed in his home state of Minnesota, James Diamond immediately picked up where his mother had left off, handling business in what could best be described as successful. Working with his team, he knew his way around the trade, quickly making his way up the career ladder impossibly fast, the next level being an actual business manager, and eventually leading to the biggest of all, CEO. With Brooke Diamond being the previous CEO before her passing, James still had to work for it, despite inheriting the business, he couldn't just take full control over it.

Gustave Rocque, a business mogul who had transformed even the shabbiest of companies, was the current CEO of Diamond Cosmetics. James didn't necessarily like him, Gustavo was an asshole, his brutal honesty being more brutal if anything. He found it so hard to believe that someone like Kelly could actually be one of that man's closest friends, but she always said that he was much nicer once you got to know him. James didn't care to do so. But he also knew that Gustavo was excellent at what he did, and he knew that the family company was in the right hands.

Apart from whatever conflict he had with Gustavo, his life had been going seemingly flawlessly. People were throwing themselves at him, whether it be to get him to help sign on to whatever project that had planned out, to trying to get into his pants, hoping to become either Mr. or Mrs. Diamond, a life of luxury surely awaiting them.

James didn't mind at all. With money and sex being thrown at him left and right, he was loving his life, until the scandal completely shook up his career.

James was no stranger to sexing up his clients. In fact, he could even get a bit ruthless at times. While most of his business contacts were elderly and just not the type James liked to bang, that didn't stop him from fucking the sons and daughters of these old snobs, with him usually cutting off contact from their once he had finished the deal with the fathers.

James took an immediate liking to Mercedes Griffin, a curvy, fiery blonde who was also making her way up in the business world. Although her personality was borderline toxic, she was very smart and persuasive, and James couldn't help but find her smoking hot, and, of course, she thought the same of him. They had hooked up quite a bit of times, with Mercedes wanting something more, and James wanting a no strings attached type of commitment. Casual sex still went on between them for a while longer.

That also wasn't his only endeavor, though. Jett Stetson, up and coming actor on the hit teen series, _New Town High_ , was currently in negotiation to be the new face for Diamond Cosmetics' newest skin cleanser, a deal which would ensure him millions for filming just a few commercial and doing a few print ads. As James talked business with Jett and his team, the brunette couldn't help but feel Jett's eyes on him the entire time. Stealing quick glances at one another, the sexual tension was undeniable.

If Jett wanted to fuck, James didn't see the issue. Even if he was a potential client, he was a consenting adult. Hell, he was a 25-year old man playing a teen on some drama, it wasn't like he didn't know what he was getting into.

And boy, James was not wrong about him. Quickly wrapping up the deal, Jett told his manager that he wanted to ask James about how to get into the "industry". What his manager didn't know was that not seconds after his lap, Jett had his face shoved in the muscular brunette's crotch, James's cock hitting the back of the Jett's throat as the actor palmed himself through his designer jeans.

It was quite a shock when the manager came back to retrieve his forgotten briefcase, only to see his client with jizz down the sides of his mouth as he told the business associate how much he couldn't wait get his "ass pummeled"", with the brunette leaning back in his leather chair, his hands behind his head, tie loosened, and pants around his ankles.

It was also quite a shock when James learned that Jett was the recently engaged fiancé of Mercedes Griffin, a woman who he had quite some history with. A woman who was also the daughter of Arthur Griffin, the CEO of the RCM CBT Globalnet Sanyoid Corporation, a potential business partner of Brooke Cosmetics who was nearly done signing off on a multi-million dollar project between the two companies.

James had unknowingly played homewrecker, as the split between Jett and Mercedes became a highly publicized event, his team working desperately to pay off anybody who knew that James Diamond, the family prodigy, was the cause of it. Trying to conduct as much damage control as possible, James's career and newly inherited company were very close to being flushed away. Deciding that transferring over to the company division in New York would be the best course of action, James packed his bags and was sent away from Minnesota with a demotion, now only an "advisor" to the other associates.

He worked hard to get his job back, which he did. Although he was back in his old position, he had taken a hefty pay cut compared to when he previously held the title. He was still making a lot of money, but his budget was a _lot_ different compared to before. New York was much more expensive that Minnesota was, and what had him living lavishly back in his home state was now keeping him living almost paycheck to paycheck.

He could always downgrade from his loft, the monthly rent cost exponential, but James would just wait it out. If he could secure just _one_ big deal, he was hopeful he would get a raise that would bump him back up to what he once was.

* * *

As he made his way back home, checking his iPhone to see that it was only a few minutes after 6:30, James was glad to finally be done after a long day at the office. He and Kelly powered through the remaining work they had left, filing all paperwork and answering all calls as the following hour had seemed to just speed by. The two said their goodbyes, with Kelly having plans with Gustavo after work and James deciding that he should rest up for the big day tomorrow.

Seeing his apartment building, he was glad to have arrived at his destination, especially before the nighttime streets became busy and impassable. As he entered through the lobby, people going in and out through the sliding glass door, the building an epicenter for those in the workforce or those just born from money, he strided along the marble floors, the sound of his dress shoes clacking against the hard stone.

Taking an elevator, he pressed the button for the 6th level, leaning his head against the wall of the cramped space, the vibration of the floors steadfastly passing him. With a ding as the elevator doors pushed back, he opened his eyes and made his down the hallway, stopping by the mailbox he and the other resident on the floor shared. Quickly gathering whatever had been delivered to him, he unlocked his door, taking in the sight of his modern, New York loft.

It was beautifully decorated, dark wooden floors you could see your reflection in, white brick walks that extended for what seemed like forever, and large glass pane windows, giving an extraordinary view of Downtown Manhattan. Hanging up his suit jacket and putting his briefcase in it's designated spot, he made his way over to the kitchen, the design scheme just as sleek and modern as the rest of his house. Leaning over the black marble countertop that had cost him a pretty penny to install, he shuffled through his stack of mail, scowling at what had been delivered to him

 _Bills_. _Bills_. _Bills_. _And_ … _**more bills**_. Sighing, he massaged his temples, knowing that he couldn't let himself form any premature worry lines. He had been careful to keep his looks youthful and attractive, with the rugged stubble and sharp, dapper haircut contrasting his still-boyish good looks. Forehead wrinkles and stress lines just wouldn't go with the character he was going for, and he wouldn't let some minor debt be the cause of any sudden imperfections.

Pushing the letters to the side, he went over to his fridge, trying to find something he could heat up and eat for dinner. He had some leftover pasta from this fancy shmancy Italian restaurant he frequented often, deciding that it would do. James Diamond could not cook to save his life, so he mostly had to rely on takeout. It was also taking a strain on his wallet, as the various expenses he made for breakfast, lunch, and dinner added up, especially when he was ordering meals every day of the week. He had no issue in taking up learning how to cook, but after the incident where he had managed to burn water, he knew that he would just have to rely on others to do it for him.

As he threw the alfredo in the microwave for a couple of minutes, he made his way over to his bedroom, his California King bed practically begging him to jump in and get some sleep. It was only seven at night, though, and James wanted to spend at least whatever time he had left this evening doing something a little more worthwhile then dozing off. Shimmying out of his work clothes, he changed into a pair of silky pajama shorts that he wasn't proud of how much he had spent on them, even if they only accentuated the v-line of his toned torso that much more. Also throwing on a grey tank top that clung to his ripped chest and abs, he put his clothes in the hamper, planning on washing them _sometime_ soon.

Hearing the ding of the microwave, James grabbed his laptop and charger, knowing he could probably waste a few hours of his night surfing the web, with his device on his lap while he ate his dinner in his underwear on the couch. Setting the electronics on the coffee table, he made his way to the kitchen, pulling the piping hot food out and opting to just eat it out of the carton, not wanting to dirty a plate.

Sitting on the large sectional couch, he booted up his laptop, entering in the password between bites of noodles that had tasted much better when they had been fresh. As the desktop popped up, his antivirus software running a scan, along with other startup programs, he set his computer off to the side, giving it a few more minutes to completely load up.

As he shoveled in the alfredo, the only food he had pretty much had the entire day, he went through his smartphone, looking to see what was new with his Instagram and Snapchat friends. Nothing important, and James didn't really find himself caring all that much anyways. Deciding that there wasn't anything else to do on it, he got up, plugging in his phone to charge by the nearest electrical outlet.

Sitting back down, he opened up his internet browser, checking his emails, looking at the latest celebrity gossip sites (hoping to avoid any articles about the Mercedes and Jett breakup, which was still highly publicized despite being a year old), and then goofing around for the next hour, looking up pointless shit that had only entertained him for a couple of minutes.

It was only eight-fifteen at night, and James was bored out of his mind. He knew what he could do, of course, it was something he did practically every night, which wasn't all that uncommon for a single guy like him.

He would watch some porn.

Not really feeling interested in any of those high-production type of videos, bad acting and fake moans sounding pretty boring to him, he stumbled on one of those live webcam sites. Well, more like typed the URL into his browser. It was a decent one, and James was a frequent guest. It had a couple of options, some girl cams, some guy ones, even couples. James was in the mood for dick, though, so his choice was obvious. As he looked through the various guys currently broadcasting, all in order from the number of viewers they currently had, he mostly just saw some twinks, a couple of twanks, and even the occasional twunk.

It wasn't what he was looking for, which was disheartening, to say the least. Especially when it seemed that 90% of the guys fit under those three categories. Nobody really catching his eye, his mouse got closer and closer to the close button on the tab.

That is, until he stumbled across a guy who was just his type, going by the username "HockeyPucker", which was in bold letters. Rapidly clicking on the preview picture, eager to get to his live stream, James was hoping that he was just as hot as he was in his profile image.

And he definitely was. He was blonde, average body type that wasn't all that muscular, body hair in _all_ the right places, thick facial hair covering the angular jawline that James just wanted to run his tongue along, and a smile that could charm the pants off of you (which was probably the whole idea of being a webcam model).

He was hot, in a scruffy, unkempt, carefree slacker kind of way. He definitely wasn't a pretty boy like most of the guys currently broadcasting, no, he was rugged, and that was exactly the way James liked it. He was currently shirtless, with his toned hairy chest on display, and from James's view, the blonde had only seemed to be wearing a backwards baseball cap. He was talking to some guy in the chat, James wasn't sure about what, but his voice sounded like music to his ears, his laugh echoing in his small bedroom as his dimples made their way to his face.

It was a good thing James didn't believe in love at first sight, because he was pretty sure he would have been in way too deep.

As the blonde held a conversation with the viewer, seeming to be actually interested in what his fans thought, James was surprised at how down to earth this guy was. Most of the broadcasters just wanted to get the show over as quick as they could, which was understandable, but Mr. HockeyPucker seemed to actually enjoy what he was doing.

Taking a quick glance over his profile info, he learned a bit about the webcam model. He was 23 years old, a non-smoker but a drinker, his bio stating that he was a musician and part-time student looking to have fun and make a few buck doing it. He seemed humble and friendly, and James could respect that. His profile also listed him as gay, which was also pretty cool.

"Haha, nah man, I won't be getting off anytime soon. It's still pretty early here, I'll probably chill for a bit and then we can get the fun started." the blonde said, smiling as he answered all the responses from the random guys in the chat box. As James saw that he only had about 18 current viewers, a pretty small number compared to the hundreds other guys could easily pull in, he was impressed with how the guy was handling it. He actually didn't seem to care about the amount of people watching him, but more so the conversation that came with it.

James had to get in on this.

He began typing up a pretty flirty message, hoping to get a positive response from the blonde and sparking a conversation between the two. As he submitted it, he was met with an error message.

" _ **Sorry, only registered members can chat with our models. Feel free to take the time to make an account!"**_

"Fuck.", James thought, hoping to talk to the guy as soon as he could. No problem, though, he could quickly make an account and get back to the blonde who held all of his interest. Making his way over to the "Register for a New Account" option, he was met with a series of questions that would take much too long to answer. What was his name? Date of birth? Orientation? His username? Rapidly typing away at the keyboard, he entered in all of his information, choosing the moniker "DiamondBoi" as his username and wrapping everything up. As he finished, he was met with a congratulations message, stating that his confirmation email would arrive very shortly.

He shoved his computer off of his lap and practically threw himself at the wall his phone was plugged into. As he unlocked his iPhone and went to his emails, refreshing the messages over and over until a new one popped up, the activation email eventually showing, the brunette sighed in relief. As he confirmed his identity, he was officially a registered member. But it didn't matter, with the amount of time it took, the blonde had probably already shot 5 loads already. Making his way back over to his laptop, signing into the website, he saw that the cam guy was still in the same position, luckily.

Getting back to striking up a conversation, he sent a message that he was hoping the webcam model would appreciate.

" _hey cutie, nice show! can't wait to learn all about you_ ;)"

As he hit reply, he could barely contain his excitement. James hardly ever got like this, but what could he say, the guy was hot. The blonde immediately noticed his response, which wasn't all that surprising, since the room wasn't very busy in the first place.

"Hey man, thanks a lot! Happy to please, what can I say. DiamondBoi, huh? Haven't seen you around before, you new?" the man questioned, readjusting his cap, his surprisingly toned arms and pits on display as they fixed the garment on his head. Deciding it was positioned right, he looked back at the camera, flashing his signature pearly whites.

" _oh yeah, just had to make an account once i saw you broadcasting. definitely the hottest guy on here!_ " James typed, feeling a shot of electricity go straight to his dick as he pressed enter. Garnering a chuckle from the model and a nod of thanks, he continued. " _guy like you must have a name… can't imagine a parent calling their kid HockeyPucker, even if it is fucking hot…_ "

The blonde laughed a bit more at this, once again repositioning himself in his chair, slightly wincing, which seemed odd to James. The chair did look pretty ratty, no doubt it must have been hard as a rock.

Kinda like James currently was.

" _Well_ , hot stuff, on here I go by HockeyPucker, gotta maintain _some_ privacy, heh. _Buuuuut_ … I suppose it wouldn't hurt to let you know. The name's Kendall, but I can always go by whatever you want it to be, man." the blonde smiled, his dimples once again forming, sending a chill down James's spine.

Kendall, huh? James loved it, it was definitely befitting of him. The name just slipped off his tongue, and he couldn't wait to flirt even harder with the blonde.

* * *

The two chatted for the next 45 minutes, along with the other few guys in the room. James learned a bit more about the kid, Kendall sharing a bit about his life, something so down-to-earth and inviting, unlike the other guys on the website.

Like his bio said, he was an aspiring musician and currently enrolled part-time at the local community college. He had a roommate, who currently wasn't at home, Kendall saying he was studying pre-med or something and was usually busy. He also loved sports, specifically hockey, and James got a glance at the backwards cap he was wearing that was emblazoned with the "Minnesota Wild" logo on the front. Minnesota was his home state, but he recently made the move to somewhere more along the east coast to pursue his musical career. He didn't say where, probably due to privacy reasons, but James had a hunch that it had to have been New York. Where else would it have been, Connecticut? Yeah right.

According to him, he was in a band with his best friend, playing some type of indie synth-pop music or something, James had never heard of it, but it sounded like it would be cool. They were just starting out, so Kendall was pretty tight on money, especially with his roommate entering such an expensive field of study. So here he was, currently selling his body on the internet.

Kendall didn't seem bothered by it, though. He thought it was fun meeting all of the people watching him.

And, oh yeah. He was a total bottom. He didn't mind switching it up every now and then, but he preferred to get fucked. **Hard**. His words exactly.

Now the fun was starting to begin.

* * *

 _ **Author's Note:**_ I'm back with a new story! A Kames one too. Hope you guys enjoy it, while I'm working on this one, I may try to whip up a couple of Kogan and Kogames oneshots/short fics too. I don't think this fic will be too long, probably not as long as Hot for Teacher was, but we'll see.

After writing the various Kames scenes in HfT, I got inspired to do a full length one. Hope you like it!

Thank you!


	2. Big Spender

_**Monday Evening, 9:36 PM**_

* * *

"So, I'm sure you guys have all been waiting for this, I mean, I'm sure my personal life can't be that interesting. I'm gonna go ahead and set a goal, can't wait to get this fucking started!" Kendall said, pumping an arm up in the air. As the guy began typing away at his computer, James could only sit in excitement. He was anxious to see just how dirty this guy could get, and when a little sound when off, he practically got whiplash from turning his head up so fast.

" _ **Tip Goal Created! At 125 tokens, I take off my shorts! Flash every 50 tokens :)**_ "

A very reasonable goal, James thought. It was a good starting point, and the price was very reasonable, too. 125 tokens was equivalent to about $12.50, an extremely cheap price compared to what other guys would charge for lesser things.

"There you guys go, let's get this show on the road! Have fun, now, don't get too excited, haha. In the meantime, let me put on some music and we can keep on chatting." Kendall said, currently scrolling through his phone, looking for something catchy to play. He decided to put on some of that indie shit James had never heard of before, but it did sound cool. The blonde continued to look through his phone, typing away at something before his head popped up at the alert.

"20 tokens! Woah, thank you so much… _CoolGuy92_!" Kendall said, pausing a bit to read who it was that had sent him the tip. "Man, I wasn't expecting to be getting tokens this soon. Thanks again! 30 more tokens left for a flash!"

James way beyond anxious to see what Kendall was packing. He never really felt himself get this way before, he would usually just kick back and watch as whatever guy was performing would speed through the goals. Kendall, however, had him on the edge of his seat. No doubt was he the absolute hottest guy to grace this website.

They various guys all went back to chatting, Kendall making small talk and answering whatever questions came him way. Some annoying user, named " _HelmetHottie"_ or something, came in and repeatedly asked Kendall to do weird shit, like feet play and other stuff like that. Kendall was very nice about it, politely declining. But the user eventually got banned from the chat room after spamming his requests without any sort of tipping.

Things went back to normal, the pace a bit too slow for James's taste, until Kendall got another tip.

"Oh hey, 30 tokens! Thank you so much "MichiganMike", glad to see one of my regulars back. Can't wait to see what's new with you. But yeah, I think you guys would all like a flash now, huh? Or maybe not, I mean, I don't really have to…" Kendall said, giggling at all of the incoming messages begging him to show something, how they couldn't wait to see that "nice dick of his". "Haha, okay guys, you know I'm not _that_ much of a tease."

Standing up, the blonde adjusted his webcam camera in order to give a better view of his full body. Biting his lips as he tried to stifle back a smile, his dimples giving it away, he hooked his thumbs into the waistband of his cargo shorts. Slowly dragging the material down as he made the " _unst unst_ " sound, his hips gyrating in a figure 8, the shorts only got lower, and lower, and lower. They slightly pulled down on his underwear, giving the viewers a peek at his happy trail that leaded down to his pubic hair. With his shorts around his ankles, he leaned over on the desk, his face in front of the camera.

"Get ready guys, this is gonna be _reaaal_ hot." Kendall said, smiling as he backed up to his original position. As he pulled down the briefs, his movements painfully slow and making James practically moan out in lust, the base of his cock became easily visible. Not even seconds later, his whole dick was in view, springing up as the briefs now reached the middle of his thighs. Taking it in his hand, Kendall began to pump it, the semi-erect shaft quickly growing harder.

"Oh shit, that feels so good. You guys like it? I bet you all do, you probably want all of it, huh?" Kendall said, his hand massaging his package, fingers wrapped around it and moving in circles, eliciting a moan from the blonde.

James was completely hard. Palming himself through his silk pajama shorts, he was finding the show to be the most erotic thing he had ever seen. Typing up a quick response, a bit hard to write one-handed, James rapidly hit the enter key, wanting to see more and more as soon as he could.

" _oh shit, love how big that cock of yours is. fucking love your body and everything about it oh god"_ James typed, letting his kinky side get the better of him. Was his sentence completely coherent? Probably not. But it sounded hot as shit.

Kendall, on the other hand, was just eating it up. "Oh yeah, you like it DiamondBoi? Bet you wanna grasp it in your hands, huh? Feel how hard I am as you rail me, right, daddy?" Kendall moaned, slowly stroking his cock until he began to smirk, pulling up his underwear slowly and teasingly. "Maybe we can get to that later." Kendall said, slightly turning to the camera, revealing that his briefs did not in fact have a backside, giving a perfect side view of his supple ass.

 _Fuuuuck_ , James thought, a jockstrap? This guy was **killing** him. As he began to type out another message about how much he was loving this, an alert suddenly went off.

"MichiganMike, hook it up! Thanks for the hundred man, that puts us way over our tip goal. Looks like I'm gonna have to ditch these shorts now, but first, I gotta create a new tip goal that I'm sure you're all gonna enjoy!" Kendall said, his grin wide as he was once again typing away at his keyboard. "As much as I love your contribution, Mikey, let's try and get some new tippers tonight! I know all of you want to see more of this."

" _This bitch_ …", James thought as he watched the smug bravado of that Milwaukee whatever user, currently gloating about being the highest tipper. Two can play at that game.

" _ **Tip Goal Created! Jack off at 200! Let's see fast we can do this! ^_^**_ "

Shit, this was exactly what James needed. As he made his way to the "Purchase Tokens" page, he sped completely through it. Selecting the highest package available, not even paying attention to the price, he quickly entered in his debit card info, messing up the first few times as he rapidly entered in the information. Finished, he was met with yet another congratulations message, stating that his account had been awarded the selected amount, and that the transaction would be processed shortly. Perfect.

"Beerdad824! Thanks for the tip dude, that's 50 tokens down! And another 50 from Mike! Holy shit guys, it's only been like 5 minutes and we're already halfways through. Nice to see the regulars back, what's up? Must wanna see me naked pretty bad, huh?" Kendall said, chuckling as he and the two regular users had a bit of back and forth banter, must to James's dismay.

Seeing that he had 2000 tokens to spend, he decided to just finish up the goal. Sending a tip of 100 tokens, showing no doubt as the computer asked to confirm his contribution, he leaned back in his chair, smiling smugly as the alert went off.

"100 tokens… from DiamondBoi! Thanks so much man, a first timer and you're already making a pretty good name for yourself. I definitely hope you become a repeat visitor, I'd love to get to know you a bit more. But now, I guess it's time for me to jack off a bit, huh?" Kendall responded, his voice getting huskier as the sentence progressed. "Gonna get rock hard, show my cock for all of you, and I'm not gonna hold back. _Gonna be awesome, guys_ …"

Leaning back in his desk chair, the blonde lifted up his legs, pulling off the colorful jockstrap in one swift motion. It happened quick, so James's didn't get too good of a look at the blonde, but he did manage to catch a peek at Kendall's ass, causing the tanned male to stifle a groan. He continued the palm his dick through the material, the heat from the close by laptop feeling good against his covered flesh. He would have started fondling himself, his precum leaking as he watched the blonde in front of him completely let loose of any inhibitions. But he would control himself, making sure to wait until the show got really good.

Once the webcam position was readjusted, the blonde leaned back, his dick in his hand as he bit his lip.

"Oh shit, I couldn't wait for this goal. Fuck it feels so good, feels like I'm gonna blow my load all over myself faster than I'd like, heh. Don't worry though, I have so much more planned for tonight…"

And he did, with James nearly busting a blood vessel when the new tip goal popped up.

" _ **Tip Goal Created! At 200 tokens it's time for some assplay! ;)**_ "

The blonde continued to stroke himself, his thumb rubbing against the head of his dick, his other hand playing a bit with his balls. Closing his eyes, humming, he looked like he was in complete pleasure. He must have been a good seven inches, James thought, a good size for when you want to get the job done. He wasn't too thick, his advantage more in length than anything, and James was certain that he had the best dick he had ever laid eyes upon.

The scene continued on for the next 15 minutes, a couple of 5 token tips here and there, along with a few considerable gifts from the two regular users.

"Yeah, is this good, guys? Fuck, I hope you all love it. Can't stop thinking about filling my ass up, any one wanna do it to me? Wanna feel my length in the palm of your hand as you go to town on me, stretching me out and making me scream your name, huh daddy?"

Kendall was just naming off a an extremely detailed list of sexual things he wanted done to him, his eyes closed the entire time, probably not even realizing what exactly he was saying. As wild as it was, James thought it was so fucking hot, his dick practically burning a hole in his pajamas as the blonde just continued with the crazy dirty talk. Biting his lip, James couldn't hold it anymore. Entering in another 100 token tip, he knew he had to get to the good stuff as soon as possible before his cock just completely exploded.

The blonde perked up at the alert sound, his eyes dilated, his body sweaty, and he let out another huge grin. "Diamond! Holy shit dude, 100 tokens again? I definitely hope you become a regular, I love you!" Kendall said, jokingly blowing a kiss at the computer screen. "Damn, I'm pretty sure this may be one of the fastest shows I've ever done, you guys must really wanna see my push my limits, huh? Well, you demand and I'll supply, baby."

Setting another tip goal, the blonde bit his lip as he did a sexy little jig, completely off rhythm to the background music, but James didn't mind at all. James sent another flirty smiley to Kendall, the guy playfully growling at the message.

" _ **Tip Goal Created! Watch me play with my ass, cumshow at 250 tokens!**_ "

Turning his back to the camera, he turned to look over his shoulder, giving a sexy little smirk. As he pulled down the jock strap down over his ass, his cheeks clenching as he shimmied out of the garment around his ankles, he let off a rough smack to his ass, causing James's cock to throb. Kendall then picked up his laptop, bringing it over the bed in the background, setting himself down on the blue comforter with his laptop directly in front of him.

"Ass play time, god it's gonna be so hot, I hope you all love it!" Kendall moaned, positioning the pillows behind him in order to give support to his lower back. Taking a few minutes to get everything settled, fixing the wires around him and adjusting the camera position, he smiled big, panting from the exertion of having to move all around for the past few moments.

Lifting his legs up a bit, he stopped once his knees were pressed to his chest. "Oh yeah, I forgot to mention. I had a little surprise going on the entire show, surprised nobody noticed it. Hopefully you all don't have heart attacks or something, haha." The blonde beamed. Lifting his legs a little bit higher, spreading them out in order to give a better view of his ass, James nearly did have a heart attack at this moment.

Apparently Kendall had had a decent sized blue butt plug in his ass for the past hour and a half. James drew in a sharp intake of breath, ripping off his shorts and taking his cock in his hand. This was so fucking hot, so fucking dirty, and James was practically in love.

With his legs in the air, Kendall began to rub circles around his hole, the close view practically causing every viewer to bust a nut at that exact moment. Kendall moaned out as his massaged his ass, his fingers gripping the end of the toy as he slowly pulled it out, his hole clenching against the rubber object. It had done a pretty good job in stretching him out, with the blonde cupping each cheek as he spread himself, James jacking himself off at what seemed like an impossible speed.

"You guys like it? Wanna see me finger myself, moaning how much I want my daddy to make me cum. Then I'm just gonna shoot my load all over myself, see how good it is. Fuck I'm so horny, wanna be your fucking whore, ngh…" Kendall moaned out, sending chills down James's spine.

He was true to his word. Having already been loosened up a bit by the previous toy, Kendall began to thrust two fingers in and out of his hairy ass. Moaning as his hole contracted from the sensation, his two digits quickly scissoring and massaging his inner walls, James could just imagine himself doing it to the blonde, completely working over his ass, getting him prepped for all of James's eight and a half inches, the thickness stretching Kendall's ass to the brim.

Adding in a third digit, Kendall threw his head back. His body was completely drenched in sweat, his skin red and flushed from the heat, his legs practically behind his head, and his hole loosening up from the motion. He threw a hand to his forehead, making it's way down south as he bit down on his clenched fist, trying to stifle out the moans and the " _oh fuck, yes daddy_ "'s that were currently coming out. James spit in his hand, going back to pumping his dick, holding back from coming just yet.

As if on cue, the two highest tippers both submitted a 50 token tip goal each, almost as if they were conversing outside of the chatroom, discussing how they could fuck James over and bring all the attention to themselves.

"Ohhhh fuck, thank you so much guys. _Ngh_ , I still feel so empty, gonna add a fourth finger in, _fuck_ , gonna fill my hole up so nice, _holy shit_ …. just 150 more tokens left, _ngh_ , _**ohfuckyeah**_ , let's see how fast we can hit the cumshow goal…" Kendall practically spat out, the sudden quick pace of the chatroom flustering him a bit.

True to his word, he added in a fourth finger, his hole stretching out even more as he rapidly thrusted them in and out, his ass getting put to work. Screaming at this point, the blonde's backwards cap having shifted, now covering his eyes, it was the hottest thing James had ever bared witness to.

"Oh god, love feeling my ass getting wrecked, _**fuck**_ , probably gonna shove my _whole_ fucking fist in next time. Oh god, _fuck me daddy_ , make me your dirty little _whore_. Want you to choke me, and, _nghh_ , make me feel so gooood…" Kendall gasped out, spitting out the last words, his breathe getting very heavy and his moans more drawn out. Clenching his ass against the four digits, the burn of the stretch making him feel like he was heaven, he barely managed to choke out what he wanted to say.

"Gonna blow my load soooo soon, oh god, somebody please get us to goal, don't know _howmuchmoreicantake_ …"

This was all James needed to hear. Feeling his own orgasm coming very, very close, he quickly entered in his tip amount, his vision hazy as he could feel the knot in his stomach. Tapping the confirmation bubble, James was met with an unfamiliar sound he hadn't heard yet during this show, the sound of coins falling and a little virtual "Woo Hoo!" calling out!

The blonde's eyes widened at the view, although they quickly closed again as he arched his back, rapidly thrusting his fingers in and out of his ass, moaning as he came all over himself, the cum sticking to all of the hairs on his stomach. Moaning out James's name, well, _DiamondBoi's_ name, he panted heavily, his eyes glossy and his smile stretched from ear to ear. James was right there with him, his load shooting out all over himself, some hitting his happy trail and some hitting his grey tank top that had been pulled up to the middle of his chest. Taking deep breaths, James let out a lazy smile, not sure exactly what had happened, but the sound of Kendall moaning his name as he came was all that mattered. Collecting the cum on his stomach and rubbing his hand on the tank top that would definitely need to be washed, James felt like the man.

" _Ohhhhhh my fucking godddd_ , holy shit! **DiamondBoi**! 1,500 tokens! Fucking A man!" Kendall yelled out, his face a mixture of disbelief and surprise, letting out a hearty chuckle as he just witnessed what happened during his show. "Dude! I fucking love you so much, nobody's ever tipped me that much!" Kendall said, his hands on his head as he struggled to find the words to say at this exciting moment.

James, on the other hand, felt his face drop. 1,500 tokens? One thousand and fucking five hundred tokens? Holy shit, what had he just done? He must not have noticed the extra zero he attached to the end of his tip note. He wanted to scream, he had just tipped the equivalent to that of $150 fucking dollars, seeing that he only had 300 more tokens left on his account. Rubbing his other hand through his hair, he didn't know what to say, barely able to type out a half-hearted " _you deserved it stud_ ", which the blonde practically screamed and giggled at.

So he just became Kendall's most favorite user ever, but at what cost? With the money troubles he was currently facing, the last thing he needed was to tip close to $200 to some random fucking guy on the internet. He was fucked.

"God damn, guys, let's give a round of applause to our highest tipper, DiamondBoi! Fuck my head is still spinning, I can't believe this!" Kendall beamed, his smile not giving the same usual effect to the guy on the other side of the computer screen. As every single user in the room congratulated James on his awesome tip, Kendall was still feeling so giddy. As he dragged his fingers through the coarse hairs on his torso, trying to collect as much of the cum as he could, he brought his finger up to his mouth, his tongue gliding all around the cum-coated digits.

" _Fuck_ , that tastes so good, but I wish it was yours, Diamond. I'm pretty much forever indebted to ya, huh?" Kendall moaned out, his fingers licked completely clean, despite the few drops of cum that had gathered on his thick facial hair. Licking his lips, he smiled at the camera with half-lidded eyes, eternally thankful for what James had just given him.

James just wished he could have enjoyed this moment a bit more.

* * *

"I knew it, I fucking knew that snake of manger that Zevon kid has would make this so goddamn difficult. Agree to his shitty terms? Does he know who James fucking Diamond is? I make the rules, it's gone this way for every negotiation I've done and he wants to sit here and completely dictate this business deal. Fuck him." James sighed, pinching the bridge of his nose as he tried to wrap his mind around the contract Dak's management tried to spring on him. He was beyond pissed at this moment, he didn't have the time to be dealing with these ridiculous demands.

"Listen James, it's not that bad. Dak Zevon is only asking for another few million, we can deal with it. The percentage of revenue he wants from the product line is crazy, I know, but we can work something out. Don't stress out, just take a breather and we can go from here." Kelly said, sitting at her desk as she sorted through the various forms that would need to be filed in order to progress with the sponsorship deal. The sound of her voice already calming the company heir to calm down a bit, she looked behind her shoulder, giving James a reassuring smile.

" _Sigh_ … yeah, I know. It just pisses me off that Hawke is trying to make it seem like we desperately need his client. Granted, _**we do**_ , but what kind of example are we making of this company if we'll just sit there and buckle under to his demands? Shit, this is so frustrating." James said, giving a half-hearted smile to Kelly to show that he truly was thankful for her help.

"Believe me, I get where you're coming from. Don't worry that pretty little head of yours, sweetie, I'm gonna head over to Gustavo's and show him everything, see if he can make any sense of it. If there's anybody who knows a thing or two about unfair contracts, it's him." Packing everything up, she checked her phone, shooting a quick reply to whatever potential contact Diamond Cosmetics had. "It's already going to be three, I'm gonna take a late lunch and then work something out with him for the rest of the day. I'll call you if we make any progress today, okay?" Kelly said, her arms full with her heavy workload, yet her face showing no signs of stress or fatigue.

"Awesome, thank you so much Kelly. I'll probably be here until seven, if anything comes up after that just shoot me a text. Good luck." James waved her off, breathing a sigh of relief once he realized that his business partner had everything under control. As the door closed, he was left alone to his own thoughts, something he was hoping he could put off until later.

* * *

It was already night time, and James was still beyond stressed out. After a brutal business meeting in which Hawke had completely grilled him, getting him to promise things he wasn't sure he could fulfill, he was just on edge the entire time, becoming more and more annoyed at each smirk Hawke gave him every time he rolled his eyes at his demands.

It also didn't help that he went into the negotiation with a clouded mind. After waking up to a pretty significant bank statement, setting him back $200 which he just didn't have, James would have murdered himself if he could. He was a fucking idiot for wasting so much money on some random guy who jacked off online for a living. He wasn't even that good looking, he was hairy and scruffy and kind of greasy, but James knew he couldn't deny that he liked it.

However, a part of James had really liked spending all that money on the blonde, finding it hot that his contributions lead to whatever sexual act it was that Kendall would perform. There was something so stimulating about it, the level of power he had over him, something that really got James off.

He didn't think it was a sort of sugar daddy complex he was going through, spending big bucks on his little plaything to make him happy. No, it was something about the control it granted him. He would make Kendall do whatever it is when he wanted, the blonde eager to follow through with it.

It was arousing for James, and he hated himself for it.

As he got ready to end his work shift, he still hadn't received a call from Kelly, no doubt the contract causing some trouble for her and Gustavo. Deciding to call it a day, he couldn't wait to get home and finally put his feet up.

He also knew that he couldn't and _wouldn't_ have a repeat performance of the previous night. Despite how much he wanted to.


	3. Two for the Price of One

_**Wednesday Morning, 9:23 AM**_

* * *

"And then I said, _"Sounds great, Bitters, a 45 year-old man living in his mother's converted garage would_ _ **definitely**_ _make an awesome financial advisor. Diamond Cosmetics would be lucky to have you!"_ , fucking idiot. I can't believe you actually made me go through with that interview, Kelly." James said, laughing as he took a sip of his mimosa, he and his assistant currently seated at an outside bistro, looking out as the mass of people passed and the cars whizzed down the bustling streets.

A look of scorn on her face, although James saw through the façade and clearly saw that she was actually trying to hold back her laughter, Kelly could only shake her head. "What can I say, I guess he must have passed through the cracks. But James, do you have to be such a jerk? And you wonder why people are so intimidated to work for this company. Perhaps _I_ should take over the interviewing process…"

"Hey, it's what I do best. And if you'd rather talk to those numbskulls, be my guest! Ha, you'd definitely be doing me a favor." James said, earning a light-hearted from eye roll from the darker female.

Conversation was nice and cheerful, as it always was. The two talking about what was going on in their respective lives, gossiping about the other workers in the building, amongst other things. They also went over the current negotiation that was going on with Mr. Zevon, a sponsorship deal that would potentially put the two on the top of the career ladder. Having worked his magic, Gustavo had found every single loophole and misworded sentence, allowing them to agree to any demands that they could later weasel themselves out of. According to head CEO Gustavo Rocque, the contract had so many amateur mistakes that Hawke practically deserved to get screwed over.

Nobody said business had to be friendly.

Seeing that it was time to get back, James signaled over a check, he and Kelly going dutch while leaving a generous tip for their waitress. Luckily their place of work was only a block away, so the two leisurely made their way to their destination, discussing all the tasks that would need to be taken care of during the course of the day.

Despite the impenetrable New York crowds, it had only taken about 15 minutes for the two to be where they wanted to be. Hitting the employee breakroom, James made his way over to the mailboxes, with Kelly whipping up two coffees for the both of them. A simple routine they found themselves in every day.

"Goddammit, still empty. I'm supposed to be expecting an important package any day now, why isn't that _Carter_ kid doing his, you know, _**job**_?" James mumbled, annoyed that his mail was _still_ being delayed, each day that passed bothering him more and more.

"Uh, James, you do know that he was just in that _horrible_ taxi accident? _**Remember**_? We even sent flowers to his hospital room, you signed the card and everything… and his name was Carlos, not Carter." Kelly responded, not surprised that James had forgotten, the business associate seemingly tuning out any stories about those beneath him in both social and financial standing.

"Oh… _right_. I guess it just slipped my mind. _Bummer_ …" James replied, a bit embarrassed that he was being such a dick to some guy who had apparently shattered every bone in his body, well, at least according to Kelly. She had been known to exaggerate, but still, pretty sad.

"We're supposed to be getting a new mail guy tomorrow, though, at least from what I've heard." Kelly said, handing James his cup of black coffee, just how he liked it. "Come on, let's get back to work."

* * *

The day was pretty uneventful. Now that the contract had been figured out, it was just a waiting game for the two, the next scheduled meeting between the two parties being the following week. There hadn't been much that needed to be done, just Kelly filing a couple of miscellaneous files and organizing the tanned male's agenda, and James answering a few calls regarding whatever shipments needed to be made for the company. By noon, the two had essentially nothing left for the day.

With Kelly painting her nails and James messing around on his phone, it seemed like the next couple of hours would just drag by.

That is, until James saw that he had received an email from " _CamSluts_ ", notifying him that "HockeyPucker" had starting broadcasting 53 minutes ago.

 _Shit_ , James thought, he couldn't just log onto the website and whip his dick out with Kelly sitting only feet away. That was gross and horribly inappropriate. He needed to get her out of here.

" _Uhh_ , Kelly, I don't think we have that much work left, how does going home early for the day sound?" James said, hoping to get to his business as quickly as he could.

"Oh, thanks James, but that's okay. I'm sure something will come up soon, but I appreciate the offer!" Kelly said, slightly turning her head to give a smile to the brunet.

"Aw, come on now Kelly, you do _so_ much work here. Why not go out and have some fun! It's only twelve, you can pay Gustavo a visit. _He is your best buddy after all..._ " James drawled out, rolling his eyes at the mention of the guy, still not seeing what made Kelly consider him her closest friend. "Maybe you guys could go shopping, or go to lunch, that sounds fun." he quickly said, mentally screaming when Kelly didn't seem to budge.

"Ha, Gustavo doing fun, normal person stuff? Don't make me laugh. Relax James, I'm totally happy here, don't worry about me. Believe me, sweetie."

Giving her an all-too-eager smile, James was getting annoyed at her work ethic. Which was funny, since anyone would love to have somebody be so enthused about working for them. In this situation, however, James wanted Kelly out of his office as soon as possible, so he'd have to be a bit passive aggressive. "I insist. Go home, get some rest, have some fun, anything. I'll probably leave early too as soon as I make a quick phone call. And come on Kelly, you do enough work around here as it is, what's one half-day?"

" _Well_ , I do have some shows I need to catch up on, so I suppose it wouldn't hurt to kick back a bit at home… okay, I guess I'll see you tomorrow then, James?" Kelly replied, packing up her stuff as James breathed a sigh of relief. Getting herself situated, she made her way out the door, saying her goodbyes to the business associate. Waving her off, James literally ran over to the door, locking it and quickly making his way over to his office desk.

Throwing himself in his leather office chair, he was more than ready to see what the object of his infatuation was up to. Rapidly typing away at his keyboard, hoping that he hadn't missed the show, he entered in the website's URL, quickly inputting his account info, signaling that "DiamondBoi" had logged on.

Heading over to Kendall's page, it showed that "HockeyPucker" was still currently online. Hoping to not have missed any of the good stuff, he clicked on his profile picture, his computer trying to get access to the live broadcast. Although it was probably just because of how anxious he currently was, it seemed as though it had taken at least a few years to get a live feed of Kendall. It wasn't because of a large amount of viewers or anything, as "HockeyPucker" currently only had 41 people watching. A nice increase from the twenty-something viewers from the last show. After a bit of buffering, he finally got a view of the blonde.

He hadn't been expecting to see a raven-haired hottie with glasses sitting next to Kendall, though.

The two were sitting on Kendall's bed, the blonde leaning back, shirtless, while the darker-haired and fully clothed male was slouched forward, cross-legged. The blonde was having some sort of discussion with one of his viewers, something about a nerdy superhero movie, James believed, while his friend was just there, looking down at the phone in his lap, seeming to be pretty uninterested.

James wanted to know more about him.

" _ **hey man, good to see you again. whos the cutie next to u?"**_ James wrote, feeling that it was short and to the point, but allowed for conversation to begin.

"So yeah, I'm super excited to see how this plays out. The last movie could have been a lot better, but oh well." Kendall said, his signature smile on display as he adjusted his usual backwards baseball cap. "Oh, DiamondBoi! Hey, welcome back man!" Looking over at his friend, Kendall shook his shoulder, pointing at the computer screen. "Dude, this is the guy I was telling you about. He tipped me, like, 1800 tokens, it was so fucking awesome!"

Looking up, the dark-haired hottie smiled, his dimples matching that of Kendall's. "Hey DiamondBoi, good to see you. Bro, Kendall here wouldn't stop talking about you, you're like a god to him, haha."

"What can I say, it's not every day some stranger on the internet up and tips you almost $200. This shitty site takes a cut so I'm only looking to get about $145 from it, but still, that's so friggin' cool, way more than I've ever made on here." Kendall said, sincere happiness on his face as he was talking to his favorite fan. Rereading his message, he answered James's question, looking over at his buddy. "Who's my friend? His name's " _Doctor Handsome_ ", and believe me, I didn't come up with it, that's for sure... Of course, s'not his real name, this loser is worried about his privacy or some shit, haha." The blonde replied, getting a light punch on the shoulder from his roommate.

Doctor Handsome, huh? The guy was cute, James thought, looking to be around the same age as Kendall, although a bit more stockier and shorter, however James could see the muscle definition of his arms, his biceps hugging the material of the white v-neck. He had short stubble on his chin, the guy going for a trimmed goatee type of look, and a neat dapper hairstyle, one that was a lot trendier and modern than that of Kendall's messy spiked-up look. His glasses didn't look dorky either.

He looked good, James had to say. He was very well-dressed, black frames on his face, his dark form-fitting jeans against his legs, the peak of his short ankle boots as he sat cross-legged, he was pretty stylish. Although he didn't want to stereotype, he was going to just assume that this guy wasn't exactly straight, so he had to wonder if he was just Kendall's "roommate".

" _ **Doctor Handsome, huh? a quite befitting name, I must say, any chance I could get a check up? ;-)"**_

Laughing, the darker-haired male seemed to look a _bit_ less uncomfortable, his semi-tense body language in stark contrast with Kendall's, who was currently scratching his armpit, not really caring that he was broadcasting on an adult webcam site. To him, this was just an average day.

Along with the other viewers, James and the two guys conversed for a good 15 minutes, both seemingly paying the most attention to the business man, no doubt because of how much he had spent on the blonde a few nights prior. Unlike Kendall, who practically gave out all but his social security number during the last show, " _Doctor Handsome_ " was a lot more private, dodging most personal questions and just giving a terse laugh or smile in return. Through Kendall's joking, he did learn that the guy was a genius, currently enrolled and excelling in a pre-med program, but from the look he gave the blonde, telling him to stop talking about it, that's all that was said on the matter. _Too_ personal.

He was also apparently a huge nerd, to which Kendall was met with a "fuck off", but Kendall reassured him that he was still _somewhat_ cool. " _Doctor Handsome_ " gave off a serious vibe, although James could see the gleeful crinkle of his eyes as he laughed at whatever stupid thing Kendall said. As the two were huddled in front of the webcam feed, both whispering to one another discussing whatever it was, possibly in regards to the show, James could have sworn that Kendall had referred to his friend as Logan, his voice almost inaudible, but the way he mouthed his name was undoubtable.

Logan, huh? A cute name for a cute guy, that is, if it really was is name.

"Okay, so _Doctor Handsome_ here has to go in about an hour and a half, so we'll try and get to the good stuff as soon as possible. Let's just start by sucking each other off?" Kendall asked, looking over at Logan who gave a nod of approval. "Yeah okay, that sounds good. I'll set it right now."

" _ **Tip Goal Created! At 200 tokens we blow each other ;) Also accepting requests"**_

As much as James wanted to, he knew he couldn't tip, unless he wanted his bank account to nearly be in the negatives. That was fine, the viewer count had bumped up to about 50 and a lot of guys were responding positively. He could hold back today, it seemed like everybody else had it under control.

Conversation carried on for the next few minutes, a 15 token tip here, a 30 token tip there, and the guys achieved their goal within 15 minutes, both smiling as they got ready to fulfill their promise.

"200 token, awesome job guys! Who knew you were all so excited to see us naked, huh?" Kendall grinned, his friend next to him mumbling a "good job" also, still a bit nervous from showing his body in such an intimate matter. He did seem to calm down a bit when Kendall said this was going to be a lot of fun. He then set a new goal.

" _ **Tip Goal Created! At 200 tokens, assplay! ;O "**_

Both guys undressing, Kendall pulling down his basketball shorts and Logan getting out of his t-shirt and dark skinny jeans, James was feeling himself get harder. Kendall was completely bare within a few minutes, turning his body so that he could give a slap to his ass, laughing. Logan was still struggling to get out of his jeans, although James got a good view of his naked torso. He had a light patch of chest hair in the middle of his two pecs, and while he didn't have a 6-pack or abs or anything like, he could still see that he was toned, especially his arms.

Finally getting out of his clothes, he laid back next to Kendall, who was already pumping his cock. Kendall was completely naked, and Logan had his boxer-briefs around his thighs, possibly feeling a bit self-conscious about showing too much skin.

James had to say, Logan was extremely hot. His dick wasn't as long as Kendall's, but it was a _lot_ thicker, and James couldn't wait to see the blonde's mouth on it. Logan also trimmed himself, unlike Kendall, who went with the all-natural hairy look, and as he took his length into his hand, James found himself doing the same, palming his already stiff cock through his dark grey slacks.

Both guys continued to rub themselves, taking side glances at one another, lazy smiles stretched across their faces. Scooting closer, Kendall pushed Logan's hand aside, now jacking him off, with Logan doing the same to him shortly after.

A mix of " _oohs_ " and " _oh fucks_ " and " _feels so good_ " were elicited by both guys, with Logan getting even louder as Kendall took his length into his mouth, his tongue lapping around the base of his shaft as Logan threw his head back, moaning. The blonde fondled his balls and looked up at him, watching his roommate's reactions as he pleasured him.

"Oh god Kendall, your mouth... _oh fuck_ …" Logan moaned, his eyes closed as he rested his hand on Kendall's head, gripping the locks as the blonde bobbed up and down, his eyes watering as he choked on the thick 6 ½ inches. He continued for the next few minutes until Logan pulled him off with a clean pop, pushing him onto his back so that he could return the favor.

Logan immediately got to work, having a bit more trouble taking all of Kendall in, mostly due to inexperience, but judging by Kendall's grunts he didn't mind one bit. The guys in the chat box were going crazy, but the two didn't seem to notice. As Logan swallowed as much as he could, his nose in the unkempt hairs, almost reaching the base, Kendall biting his lip and breathing heavy, James was completely losing it.

Undoing the cuffs of his shirt, rolling the sleeves up to his elbows and loosening his tie, James pulled the zipper of his slacks down afterwards, the dark fabric falling to his ankles as he desperately pulled his dick out of the slit of his boxers and made contact with his twitching cock, the precum making use as lube as his hand went up and down the 8 ½ inches, the brunet groaning as he watched the two friends perform.

Kendall and Logan then realized that the tip goal had been accomplished minutes prior, apologizing for not noticing, Kendall laughing and Logan's mind still reeling. Pulling each other in for a kiss, it was sloppy and desperate, teeth gnashing as Kendall held his hand to Logan's chin, the other guy with his hand on the blonde's lower back.

Kendall pulled away to type on his computer once again, setting a tip goal that James nearly lost it at, and Logan leaned back, his dick in his hand once again.

" _ **Tip Goal Created! At 450 tokens we flip fuck! :D"**_

James slowed down as he thrusted his dick in the palm of his hands, wanting to hold his orgasm off until he actually got to witness the best part.

As they readjusted the webcam camera in order to give a better view, they decided that it was close enough for their viewers to see what was going on, the quality beautiful and crystal clear. Kendall must have paid good money for such top notch equipment. James had to wonder how much of Kendall's income relied solely on sex work.

The blonde was surprised when Logan flipped him over, commanding him to get on all fours. Kendall of course obliged, his ass up in the air, excited to see what Logan would do to him. Logan was in full control, suddenly becoming demanding and dominant, something James wasn't expecting. If Kendall was a power bottom, Logan must have been a power top, although it appeared the boys did switch off occasionally.

"You all ready to see me work this little bitch's ass?" Logan said, half-joking, which earned a laugh from this blonde. Pretending as though he was gonna put his whole fist in there, Logan eventually settled down and began to get to what everybody was waiting for. Spreading his cheeks, the blonde's hole on display for all 53 viewers, Logan gave a rough smack to his ass, earning a pleasured yelp. With one hand cupping the blonde's ass, his other hand went to the blonde's mouth, Kendall sucking on each digit, wanting to get them as lubed up as he could. "Oh fuck, wanna feel them so deep, come on man, do it already…"

Not one to disappoint, Logan started off with two fingers, the blonde used to having things up there. As he pumped his fingers in and out, stretching and scissoring his hole, Kendall clenched tight against him. The blonde was a mess, moaning and groaning as his ass was being worked over, his face pressed into the bed as he tried to contain his screams. "Oh god, fuck me, fuck me, harder, harder."

Logan added a third digit in, the blonde's legs quivering from pleasure as he worked him over. Logan eventually pulled out and stopped, Kendall's ass clenching and trying to grasp against anything now that it was empty. The blonde looked up, smirking now that it was his turn to pleasure his friend.

Looking as the computer screen, he saw that the tip goal had once again be cleared, surprised at how fast it was going. "Oh fuck, thanks a lot guys. Can't wait to rail this fucker's ass, haha." Kendall said, giving a rough slap to the paler guys ass, Logan giving him a look in return that was a mixture of "fuck _you_ " and " _fuck_ me".

Logan was on his back, his legs in the air as he gave the camera a good look at his hole. His ass was a lot smoother and fatter than Kendall's hairy flat one, and James could only describe it one way: ridiculous. Kendall pulled in the webcam for a much closer look, with Logan's ass taking up the majority of the screen, along with Kendall's face.

The blonde grabbed each cheek, massaging them and squeezing them, his fingers leaving red marks on the creamy skin. Craning his neck forward, he gave a long swipe against Logan's ass with his tongue, already causing the other guy to moan. Darting his tongue, the muscle making swift motions all around his roommate's hole, his thick facial hair rubbing against Logan's sensitive ass, only making him that much crazier, James almost blew his load right then and there.

"Oh fuck, _ngh_ , just like that Kendall. _Fuckitfeelssogood_ , _**gah**_." Logan moaned, whimpering as Kendall pulled away so that he could retrieve the lube from the nearby end table. As he returned, popping open the cap and squeezing the cool liquid on his fingers, he began to prep Logan, starting off with a single finger.

Logan was fine, although it felt odd to him, he was ready for the real thing. Seeing that he was relaxed, Kendall added in another finger, slowly going in and out, the brunet tensing up, trying to relax his body once more. Kendall worked his fingers in Logan's ass, massaging his inner walls, eventually finding the spot he was looking for. Judging by the cry of pleasure Logan had elicited, Kendall continued to rub against the area, only to stop every once in a while so that he could plant a kiss on the raven-haired guy's lips.

Deciding he was prepared enough, Kendall moved away from Logan, adjusting the webcam in order to give a side view of the two males. With Logan's ass slightly hovering above the edge of the bed, Kendall got in front of him, slicking his dick up with a bit more lube. "You ready? Tell me how it feels, you're in control." Kendall whispered into Logan's ear, his roommate lazily nodding his head. Lining his dick up with Logan's hole, he pushed in slowly, his friend taking in a sharp intake of breath, Kendall stopping right then and there. Taking a few moments to adjust, Logan gave Kendall the okay, the blonde once again picking up speed, slowly but surely getting his entire length in the guy, the process taking quite a bit of time. Too much time, in fact, for James.

He was gentle at first, his dick filling Logan up to the brim, with Kendall slowly rubbing circles on his roommate's upper arms in order to get him to relax.

"Fuck, go faster, I'm ready for it, ngh, don't fucking stop…" Logan said, one arm behind his head with his other jacking himself off. Taking his cue, Kendall's pace quickened, the sound of his balls slapping against Logan's thighs growing louder, the blonde pulling his friend's legs over his shoulders, allowing for deeper access. " _Ohshitjustlikethat_ , fuck me, oh fuck it's so big…"

The two boys were working up a sweat, Kendall keeping a good rhythm as Logan's hole held an iron-clad grip on his length, his tight ass feeling amazing to the blonde. He was getting pounded, his glasses slightly askew, with the bed springs sounding like they would explode any second.

James continued to pump his cock, spitting into his hand to add to the sensation. He could just imagine himself there with them, watching the two fuck each other, tiring one another out. After both had came, cum all over their bodies and faces flushed, it would be his turn, switching off between the two men, the tightness of their asses feeling amazing. He'd pay special attention to the blonde, showing him exactly what daddy had in store for him. It sounded so fucking amazing, James almost came right then and there. Almost.

"Oh fuck Kendall, it's my turn now. Can't wait to feel that ass of yours, gonna make you beg like a little bitch." Logan growled, his dominant nature once again coming out from within him. Smirking, the blonde pulled away, gesturing a come hither motion to the genius. Once again meeting for a sloppy kiss, their erections rubbings against one another, Logan whispered something in Kendall's ear, something that made him wide-eyed and grinning from ear to ear.

Logan began to readjust the camera position this time, pulling the webcam on top of the bed, giving a much closer view of what was to come. It took him a while to get the positon perfect, also making sure that it was completely focused. In the background, Kendall, however, had one hand against the headboard and his other one currently occupied, his fingers rapidly moving in and out of his ass, stretching himself out again for what was next.

Deciding it was good enough, Logan threw himself on the bed, lying on his back as the blonde crawled over to him. Hovering over his lap, Kendall got himself situated, pouring a small amount of lube onto his hand that he rubbed over his hole. Closing the bottle and tossing it to the side, he lowered himself down, Logan's dick sliding in with ease. He sat for a moment, taking in the new sensation of being filled. Unlike Logan, however, he hardly needed time to get used to it, immediately picking up the pace and slamming himself down on his roommate.

It was a lot faster paced, Kendall's gyrating his hips against his roommate's crotch, Logan rapidly thrusting into the blonde's hairy ass, squeezing his cheeks and spreading them out, fucking him deeper and deeper with each thrust. Kendall was loving it, the dirty talk coming into play, as he was much kinkier than his raven-haired friend.

"Oh fuck that feels so good, fuck me so hard, _oh shit_. Work it baby, fucking destroy me, make my ass yours." Kendall screamed, the only sounds echoing throughout the room being his moans, the creaky mattress, and the sound of skin against skin. Unbeknownst to them, guys were tipping left and right, saying how much they loved seeing "that little slut giving up his ass".

Kendall was docile in nature, being generally laid back and go with the flow. But it seemed that when he had a dick up his ass, he was a bossy little power bottom, shouting out all the stuff he wanted, _no_ , _**demanded**_ Logan to do to him. He was going on and on about how much of a "whore" or a "messy little bitch" he was for Logan, the genius only grunting in reply.

James wasn't used to somebody being so vocal during sex, saying exactly what it was that they wanted, and it was only turning him on more and more. Fuck the webcam, he wanted Kendall in person, the blonde telling him how much he wanted daddy to raw him, to mark him as his own. Feeling his own orgasm nearing, James was feeling a light-headed, his sole attention being on the view in front of him. He wasn't sure what it was that came over him as he rapidly clicked the "Buy More Tokens" button, his account and credit card info already saved in the system, making things easier for him. He didn't care, though. He wanted the two guys to know how much he loved it. He wanted Kendall to know.

" _ **DiamondBoi has tipped 2200 tokens!**_ " flashed across the screen, the " _WooHoo!_ " and raining token sounds that specifically designated an extremely large tip catching the attention of the two broadcasters. Logan immediately stopped thrusting, and Kendall looked over his shoulder, not really realizing what had happened, both of their heads spinning from the current session. Kendall, however, barely managed to find the words to say, the blonde in complete shock.

"Fuck! Oh my _fucking_ god DiamondBoi, holy shit, _holyshitholyshitholyshit_. Thank you so much, I don't even know what to say. **Logan**! Look, he did it again, I can't believe this!" Kendall practically yelled out, clapping along with all of the other viewers who were congratulating James on his contribution, and also Logan, who was seemingly speechless, a crooked smile stretched from ear to ear. In the heat of the moment, Kendall accidentally confirmed that his friends name actually _was_ Logan, but the two didn't seem to notice the mistake, it was pretty insignificant at this point.

"Phew, okay, that was so friggin' crazy. DiamondBoi, let's do a private show later on, you definitely deserved it. Now come on Logan, get back to what you were doing to me." Kendall moaned, throwing his ass up and down as he got back to business.

James was pumping his cock at full speed, a feeling of euphoria as the guy in front of him just practically promised he would do whatever he wanted for him. As he pleasured himself, his thick dick in his hands and his head thrown back, he felt like he was in his own little world. Now was about the time that the window cleaners usually washed his glass office from the outside, but he didn't even care if they saw what he was doing, or what was on his screen. The only thing that mattered right now was the blonde and his cute little friend.

"Oh fuck, just like that Logan, fuck I'm so close, fucking fill me up, breed my ass baby. Oh god, just like that, I fucking love it!" Kendall screamed, his hole clenched around Logan's thick cock, the ring of muscles feeling like heaven to the genius. Kendall slightly turned his head looking directly into the camera, his face flushed, his entire body drenched in sweat, the coarse hairs all over his skin matted down, he looked like a mess, and James loved it. "Oh fuck, _Logan_ , I'm gonna cum, I'm gonna fucking cum. _Ngh_ , this is for you, _DiamondBoi_ …", Kendall said, giving the camera a wink.

James was lucky he hadn't had a stroke right then and there.

With that, he shot his load all over his roommate's chest hands free, the sensation of being anally penetrated and his prostate being stimulated over and over more than enough to set him over the edge. Logan followed shortly after, unloading his cum deep into Kendall's ass, the blonde moaning as he rode out the last few thrusts, the genius moaning Kendall's name.

That was it for James. With a groan, he came all over his dress shirt, thighs, boxers, and hand, seemingly having shot the biggest load of his life. He skin also sheened with sweat, his cheeks rosy as he still thought about what he had just seen. It was so erotic, the amateur value to it making it feel that much more realistic and personal. The realization that he had just dropped another $200 on the guy hadn't truly dawned on him yet, but it surely would much sooner than later. He did, however, immediately notice the mess he made, cum splatters obvious on the different articles of clothing he was wearing.

His underwear and dress shirt were a mess, most of the cum having landed on the two fabrics. He wiped his hand on the bottom of his shirt, figuring he would be able to cover it up with a buttoned up suit jacket. The boxers were a bit more noticeable, but he hoped the few small spots wouldn't leak through his slacks. He put that situation off to the side, though, it wasn't very important at this moment.

Kendall pulled off of Logan, ropes of cum spilling out of his ass, the blonde trying to recollect his breath. He wiped up the cum from his roommate's torso, bringing the bodily fluids to his mouth, only to swap them between the genius with a kiss. As the two made out, both dicks now growing softer, the broke apart, smiling from the past events over the last hour.

Wiping the sweat from his forehead with the back of his arm, his breathing still irregular, Logan in the background cleaning himself off, Kendall gave a smile to all of his viewers. "Thank you guys _sooo_ much for all the tips, I love all 'a you. And special shout out to Mr. Diamond, holy shit you really hooked it up. Get in contact with me, my info's in my description, I wanna work something _special_ out with you. _Fuck_ that was great… okay, I'm gonna go, see you guys soon, and… shit, thanks once again guys."

" _ **Broadcast has ended"**_


	4. Night Like This

_**Thursday Afternoon, 1:13 PM**_

* * *

"Kelly, do something about him! That _creep_ won't stop calling and emailing our company handle, he was even waiting outside the goddamn building this morning with an iced coffee he bought just for me. Which was delicious, by the way… But I don't know how much more blunt I could have been. It's honestly just pathetic of him at this point." James groaned, pinching the bridge of his nose as he only became more annoyed as the day progressed.

"James, I already told you I tried talking to him, but he just won't budge. Listen, just ignore him, Bitters will take the hint eventually. If worse comes to worst we can just file a restraining order or something, but in the meantime he's the least of our concerns." Kelly responded, taking a bite of a muffin that was part of a gift basket delivered to James, the note card being addressed from ' _Reginald Bitters, a friend and an asset :)_ '. "Or you can just keep on stringing him along, these are _really_ good."

Seeing as how he was already working on his third one, he had to agree. James was a bit worried that he would go over his daily carb intake, but he supposed it wouldn't hurt to let himself have a cheat day.

Regardless, it was annoying having to deal with somebody as annoying as that guy. He was tired of playing nice. Well, Kelly was playing nice, James on the other hand ended up telling Bitters that he was a loser who would die alone. He felt it was called for, seeing as how he only bought the brunet a medium coffee. James Diamond only does large.

Sighing, he picked himself up from out of his chair, getting up to throw his trash away. Remembering what Kelly had said about there being a new mail courier today, he figured he would check to see if his packages had finally come, the documents within it being crucial to his current negotiation. Making his way over to the employee breakroom, he was glad to see that the mess had been cleaned up. All the mail was finally where it should have been, the stacks of paper that had been scattered all around the tables and floors finally finding a home.

Luckily, the items he had been expecting had been delivered, so he and Kelly would just need to sort it out and get everything finished. He also noticed that a 20% off coupon to _Bath and Bodyworks_ had been taped to the front of his mailbox, the only person who could have attached it being obvious. He tossed it to the side, not paying any attention to it. When he turned his head, however, he saw what he assumed to be the new employee.

He only got a view from the back, and James liked what he saw. The guy was tall, probably only a few inches shorter than himself. He was wearing a light blue short-sleeved dress shirt with light khaki pants, the fabric flush against the skin of his seemingly flat ass. That wasn't a detractor for James or anything, though. The guy was still hot looking, from what he could see.

When the new mail clerk turned around, though, James practically lost his breath.

It was him. The big nose, the thick facial hair, the carefree styling of his hair, the piercing green eyes, the dimples that formed as he smiled upon seeing the brunet. James was standing face to face with _**him**_.

"Oh! Hey man, do you need anything? I've been organizing this shit all morning and I think that's everything. Did you get all your mail?" the blonde asked, a bit confused at why the older male was just staring at him like that. "Dude, are you okay?"

James was more than okay, he was fantastic. Here he was, the guy he had been obsessing over for the past week, standing in front of him in all his glory. He was ecstatic to see the man, wanting nothing more than to grab him by his brown and white striped tie and pull him in, smashing their lips together as the brunet told him all about how crazy he had been driving him.

That would be unrealistic, though.

It was funny the way the mail clerk talked him, his lack of professionalism as he referred to James, his superior, as some buddy of his. The brunet found it endearing, however. It made the blonde seem so much more approachable and friendly. _And also sexy_.

"Hm? Oh, _yeah_ , just admiring the handiwork you did here, the office looked like a bomb went off before you were hired. Last guy was horrible." James responded, setting his hand out in front of the blonde, and he was met with a firm handshake, the two beaming at one another. "James Diamond, charmed. And _you_? Got a name, blondie?"

"Kendall Knight, great to meet you _ma-I mean_ , sir. I really appreciate it, everyone here is so nice. Wish I would have applied here sooner!" Kendall said, laughing. James joined in, not finding it particularly funny what he had said, but he was a sucker for dimples.

"I gotta get going, I'll let you get back to work. You seem cool, how about I buy you lunch one of these days, Kendall? Tell you all about the things that go on here?" James said, his hand leaning against the doorframe as he cradled his package in the other arm.

"Dude, that sounds really cool. Heh, you treat all of the mail clerks like this?" Kendall smiled, looking down as he shuffled through the stack of letters he had in his hand.

"Only the hot ones." James smirked, turning his back as he walked out of the breakroom, a quick side glance giving view at a very flustered Kendall who had dropped the mail he held in his hands.

This would be way too easy.

* * *

As he made his way back over to his personal office, ready to get to work with Kelly, he couldn't stop thinking about what had just happened.

Kendall, of all people, was the new mailroom clerk.

Was it a gift from the gods? Was lady luck on James's side? Did he have a bout of good karma? Whatever it was, James wouldn't question. The situation was just too good for him to over analyze.

Things would practically fall into place, James had Kendall like putty in his hands. It wouldn't take long, he'd take the blonde out for lunch, chatting over their meal as James learned _all_ about him, remarking about how down-to-earth the guy was. He'd flirt a bit, maybe press his knee against his, and in no time he'd have the blonde in his bed. He'd done it so many times before that it was practically a ritual for the business man.

He did the same thing with the head secretary of their division, Camille Roberts. She was a feisty little thing, James had to admit that she was a lot harder to get than the others, the brunet having to shell out a pretty penny to woo her. It was so worth it, though, the curly-haired beauty was one of his best hook ups, the way she moaned his name sounding like sweet, harmonious music.

She was just a quick fuck, though, the two hadn't talked again after that. There weren't exactly hard feelings, but she did act awkward around him the following day, stating that she had somewhere to be whenever he was in close proximity. That was okay with James though, there were plenty of fish in the sea.

Like Kendall. Although he wasn't sure if he just wanted this to be a one-time tryst between the two. Something about the blonde just sent him reeling, and James wanted to figure it out.

Whatever it was, he would go about that path later. There were more important situations to tackle, like the ongoing deal between Diamond Cosmetics and Zevon's management. They needed to get some last minute written agreements filled out before their meeting the following week, and while it wouldn't necessarily need to be a lot of work, James and Kelly would need to read the attachments word for work, making sure no little additions to the negotiation were sneaked in.

Opening the door, Kelly taking an immediate notice to what James had in his hand, she turned her chair around, ready to get to business.

"Good, they finally came! I assume our new mail clerk arrived today, thank god. That place was beginning to look like a disaster." Kelly said, grabbing a nearby boxcutter to rip through the cardboard. "I heard he's a nice guy, kinda cute too, Kendall I believe? Apparently his résumé was just a picture of some famed athlete, but I highly doubt that, you know the stories that circulate around here."

Although it was funny if it was true, James would be a bit embarrassed if it really was what secured the blonde his job. Granted, a mailroom clerk was hardly one of the most challenging jobs, the toughest of the qualifications being basic literacy. But it would be a new low for Diamond Cosmetics if they were that desperate to hire somebody for the open position.

"Yeah, he seems okay. Would have pegged him as the slacker type, but he really busted his ass organizing those heaps of mail." James replied, leaning over Kelly's desk as the two made sense of the files in front of them. Sighing as he saw the work load the two would have to try and get accomplished before next week, leaving them hardly any time to get everything completely done, he knew there wouldn't be any time for leisure. Wooing Kendall would just have to wait.

The duo immediately got to work, reading through the hard to understand legal jargon and various terms neither had ever heard of, James and Kelly were ripping their hair out by the second hour. It was almost 4:30 and they had barely put a dent in the pile of forms, so they decided to each take half home, with Kelly going to Gustavo's and working on the legal documents while James went to his apartment and completed the various insurance forms, terms and conditions, and any other agreements.

* * *

"That's awesome, thank god it didn't cause you guys too much trouble. Give Gustavo my regards, I gotta give it to him, the man knows what he's doing." James said, leaning back against his sectional couch, his phone resting in the crook of his neck as he spoke to Kelly on the phone. It was already 12:30, James gazing out his windows as the lights of the skyscrapers painted along the dark backdrop of the city illuminated his living room. Kelly had finally gotten her part of the work finished, Gustavo once again proving to be a huge asset to the ongoing deal.

As James hung up, saying his good nights to his assistant, he threw his phone haphazardly across the cushions, sighing as he saw the piles of papers surrounding him, covering every inch of the couch and coffee table. He only had about a quarter of the work remaining, but he could have finished a lot longer ago had he stayed focused. While his laziness had played a huge role in his failing to do so, there was a certain somebody that had occupied his thought every now and then.

He still couldn't believe that Kendall, the guy he had spent hundreds on, the guy he had tossed virtual money at in return for pleasuring himself on camera, had now become the 24th floor mailroom clerk of Diamond Cosmetics. Was it a coincidence? Possibly, but James was chalking it up to something a bit more hopeful, like fate. He'd have the blonde in no time, breathing heavy under him as he slammed the poor kid's brains out, the husky groan of James's name on his lips. James had always been a noncommittal, bachelor-lifestyle living kind of guy, the brunet not being much a fan of monogamy. Maybe Kendall could change that, though? The thought didn't bother James as much as he thought it would.

Was it unrealistic? Sure, but at the end of the day, James Diamond always got what he wanted.

* * *

 _ **~ One Week Later ~**_

 _ **Thursday Evening, 5:19 PM**_

* * *

Needless to say, the meeting between the two parties went without a hitch. Hawke was thrilled that Diamond Cosmetics had fully agreed to his conditions, James plastering a fake smile as he hid the fact that his company had already found every hole in the contract, knowing that the ridiculous demands, like "70% of all royalties", wouldn't need to be fulfilled. Hawke completely screwed over his client, but James didn't feel an ounce of remorse. Dak would be getting a cool couple of million, that was more than enough for a few print ads.

Plus, he should have found better management.

After the success that Monday held, James was flying high for the rest of the week. While he still had a few more tasks left for the negotiation, teen heartthrob Dak Zevon, being the new face of Diamond Cosmetics, was essentially a done deal. Him and Kelly celebrated over drinks immediately after work had ended, bringing Gustavo along, seeing as how the whole thing had been his doing.

While of course it was a major win for the company, it was even more so a greater celebration for the business associate and his assistant. Signing on someone with as much influence and star power as Dak had was sure to make a name for the two. It wouldn't be much longer until James got a hefty promotion and raise, with Kelly also getting her share of benefits.

Work that week had been pretty laidback thereafter, the duo finally able to take a much needed break. Kelly's brother and his wife had just had their baby the day after the business deal had been completed, so the assistant was luckily able to go down to Florida and visit the two. She took a short-noticed two week vacation off from work, but it hardly interfered with anything James and Kelly had planned. She had really put her all of her effort into her work the past few months, so a short leave from the company was more than deserved.

James, on the other hand, still had some things he needed to do. Now that the contract with Dak was close to being finalized, he would need to start another project shortly after. Although he could afford to take it a bit easy for a while, it didn't mean that he could just slack off. As he spoke to the management team of Jo Taylor, breakthrough actress of the hit show " _New Town High_ ", he had a feeling that this negotiation would go a lot smoother than the previous one had. Jo's agent was a lot more agreeable and realistic, something James could appreciate. He felt a sense of accomplishment running throughout him as he handled the matters on his own, not having to rely on Kelly for helping him with the brunt of the work.

While James worked on that throughout the next three days, he also began to talk to a certain mailroom clerk a lot more. And by talking, he actually meant nonstop flirting, something the blonde wasn't shy to and often reciprocated.

As James made his way over to the breakroom to "check his mail", despite having already done so six times within the past eight hours, he smirked as he saw Kendall with his back turned from him, undoubtedly tapping away at his cell phone despite him being on the clock.

Kendall was a bit of a rule breaker here at the office, but management hardly cared. He was just some lackey who organized mail, and he was damn good at it, too. Playing games while on the job was hardly that big of a deal, as long as he accomplished what was asked of him.

Another advantage was that it gave them time to interact.

As James stood in front of his mailbox, making a "tsk" sound as he saw that it was "surprisingly' empty, he caught the attention of the blonde, who turned around and shot him a smile.

"Oh, hey James. Sorry man, nothing else came for you today." Kendall said, stuffing his phone into his pocket as though he hadn't just been obviously using it. It was funny to see how laid back Kendall was with the brunet, the two apparently being on a first name basis, despite the majority of the floor all referring to him as Mr. Diamond. James hardly cared, though, Kendall could call him whatever he wanted to. Especially if it had a sexual connotation to it.

"Damn, how about that. Oh well, I guess I'll just go and wait over in my office, but I don't really have anything to do… I'm probably gonna clock out in a bit, so I guess I can just hang with you for a bit?" James said, a crooked smile on his face as Kendall raised an eyebrow at him. "Unless, of course, you're busy. Wouldn't want to distract a working man like _you_."

" _Actually_ … I'm getting off pretty soon, and I was just about to go on my break too. Well, _second_ break. The company doesn't need to know that, though." Kendall laughed, watching as James leaned against the wall, suit jacket thrown over his shoulder as he listened to him with full attention. "You know, I think I recall you offering to buy me something to eat, is the deal still good? I know that lunch was part of the offer, but maybe I can exchange that for dinner instead? I know how you business men are with contracts and whatnot, after all."

"I suppose I might have mentioned something along the lines of that. We can head to this awesome restaurant, _Chez Fancee_ , it's real swanky and the food is beyond delicious. How about it, blondie?" James responded, his voice smooth and alluring, the mailroom clerk smirking as he nodded his head.

"Or… we could do burgers? I know a cool little hole in the wall a few blocks away, they have the best onion rings in the world. Assuming that's up to your standards, of course." Kendall said, fast food being more than enough to satisfy him. Needless to say, he was hardly a frequent guest at any French cuisine type of establishments. Especially on a minimum wage salary.

"Sounds perfect."

* * *

The two traversed across the busy streets of New York, bodies pressed relatively close against one another, mostly due to the packed space from all the pedestrians moving to and fro down the sidewalk. James wasn't complaining, though, if anything it only worked out in his favor.

Conversation was light between the men as they walked. The occasional joke was made along the way, whether it be about whatever shady person was hawking bootlegged goods on the side, to the street performers in dirty, cheaply made costumes, obvious tourists taking pictures with them. Apart from that, a comfortable silence fell between one another as each guy was left to their own thoughts.

"Oh look, we're here!" Kendall said, pointing out a little shop with a large neon sign, the business apparently called " _Buddy's Burgers_ ", one of the D's on the sign having burned out. It really was a hole in the wall, wedged in between a laundromat and some type of floral arrangement store. James trailed behind, noticing all of the blue-collar workers and smiling families of four grabbing a late night bite to eat, feeling a bit out of place as he strolled in with his Armani 2013 collection suit and slick, dapper hairstyle, James Diamond fitting the bill of a rich spoiled brat.

Kendall, on the other hand, fit right in. From the scruffy beard and disheveled hair, to the green sweater vest over his white shirt, dark blue dickies, and a black tie finishing off his outfit, he looked like your average joe. Something James found so appealing.

They put their order in, two double cheeseburgers with sides of onion rings, which Kendall once again mentioned being the best, and while the blonde opted for a large chocolate milkshake, James went with a small diet coke. He'd have to hit the gym hard over the weekend if he wanted to burn off the calories, but he would think about that later. His main focus tonight would be on the guy standing next to him.

The inside was packed, each booth being occupied and all chairs taken, although the two were lucky to find a currently vacant table outside, the sky overcast and becoming darker, a chilly breeze in the air. There was a gas lamp next to them, so the warmth radiating from off of it definitely helped. The each took a seat, Kendall placing the electric coaster that would notify them that their meal was ready next to the umbrella, looking up at the brunet, testing his reaction.

"So? What do you think so far? Is this place awesome or what?"

"It's very, uh, _cozy_ , I guess… Not too bad, assuming the food isn't shitty." James responded, the blonde giving a light chuckle at his comment. "Even though I feel like a stick in the mud here, it looks good so far man. Perhaps I'll hit this place up again later on."

"And perhaps I'll come with?" Kendall said, raising an eyebrow as the brunet gave him a smirk. "You'll love it though, promise."

" _Heh_ , we'll see about that… so Kendall, I didn't just buy you dinner so that we could talk about how cool this place is for the next hour. Tell me about yourself, I hardly know anything about you."

"What, me being a mailroom clerk isn't interesting enough?" Kendall replied, looking down as he gave out a laugh. "Wow, let's see. When I'm not at the office, I'm currently enrolled part-time at the local community college, Monday and Wednesday nights. What else, uh, I don't live too far from here, me and my best friend renting a Brownstone. He's in school too, kind of a square but he has his moments. Oh! I'm actually a Minnesota native, I just moved here to New York, like, almost a year ago I believe."

"No way, I'm a Minnesota boy too! Minneapolis, you?" James said, his suspicions correct when he had seen Kendall wearing the Minnesota Wild cap from before.

"Duluth. But that's still cool! Why the move?"

"Oh, just for business. The New York division was becoming a bit more lucrative so I came over here to help out, and, well, here I am." James said, leaning back in his chair with an elbow propped up on the table, all attention diverted on the guy in front of him. "But college, eh? That's real cool man, what major? I'm guessing you don't wanna be a mailroom clerk forever?"

"Well, assuming that my plan of becoming an Upper East Side widower to my late, wealthy husband named Richard doesn't work out, I'd love to work in the music industry." the blonde said, confirming that he did indeed bat for the same team. James hadn't had any doubts about it, though.

"In Minnesota it was always hockey, hockey, hockey, and don't get me wrong, I definitely loved playing it. _But_ … I don't know, I guess when something is forced on you _so_ much, you kind of want to distance yourself away from it." Kendall said, James nodding his head in agreement. "Music had always been kind of a side project, so once high school was over I was able to actually venture a bit deeper into it. Figured a place like the Big Apple would be a safe starting point. Me and my friends have a band, which honestly hasn't even begun to take off anywhere, but I don't care. My mom and sister are definitely supportive, so we'll see where this goes."

 _ ***BUZZBUZZBUZZBUZZBUZZ***_

"Oh hey, looks like the food's ready. Stay here, I'll go and get it, it's only fair seeing as how I dragged you here and let you pay for all of it. Back in a bit." Kendall smiled, taking the vibrating coaster with him, disappearing as he walked into the building, James turning his head away to watch the glowing city lights in front of him, a light drizzle picking up, the reflection of the skyscrapers on the wet roads.

James was fascinated by the blonde. Conversation had mostly consisted of stuff he had already heard Kendall talk about online, James pretending as though it had been the first time hearing it. But listening to it firsthand, as he saw the glimmer in the guy's eyes as he described his life to somebody who was truly interested, James could just feel himself being sucked in.

To be honest, the brunet had just been looking for a quick hook up with the blonde, wanting to live out all of the ideas he had fantasized about him for the past few weeks. But the two actually hit it off, James actually being interested in what he had to say, as opposing to just staring at his chest or package as he had done to the countless others.

Was he thinking about a relationship? Fuck no, that was never going to happen. The two men had completely differing views of the world and how they wanted to live in it, not to mention the 11-year age gap between 34 and 23.

He had a feeling it was a just matter of lust over love, if anything.

Although it was yet to be brought up, there was something he'd have to confess to Kendall sooner than later, with what he had done over the past few weeks nagging away at him. He had spent hundreds of dollars on Kendall via online transactions, watching as the younger guy got himself off for people to watch. It was an awkward thing to bring up, part of James considering never doing so.

What could he really say? "Hey Kendall, you're right, these onion rings are awesome! But not as awesome as that time I watched you put stuff up your ass online."

Well, he could, but he wasn't sure how well that'd turn out.

"And here we are! Smells delicious, right?" Kendall said, setting the tray of food down in between them, gauging the business man's reaction, grinning when he the brunet unconsciously licked his lips. "Ha, knew it."

Splitting the servings up between them, the two falling into conversation once again as they ate their dinner, they talked about random topics. Music, TV, famous people James has met, small gigs Kendall had played here in New York. It was nice, it was comfortable, it was unsettling for James as he felt himself pushing away the idea of just wanting a quickie out of the blonde.

Looking at the outside world, Kendall took notice of the sudden change in weather. "Fuck, it's already pouring! I didn't hear anything about rain tonight, and little ol' me is without an umbrella." Kendall laughed, looking down at his chest as he used a finger to wipe off the glob of thousand island dressing he had spilled on the front of his sweater vest, a large noticeable stain now present that the blonde just shrugged off.

The two had finished their food half an hour ago, having spent the rest of their time just chatting. James had successfully given Kendall his phone number, telling him that having a " _powerful business contact_ " readily available could help him out one day. The blonde didn't buy it, chuckling as he thanked James for the " _opportunity of a lifetime_ ".

"Yeah, it's really coming down, who would have thought." James responded, checking his phone and saw that it was already 8:32 at night. "Oh man, I can't believe it's already this late. Wanna get out of here? It's raining too hard to walk back, especially without an umbrella. Plus, I don't want to fuck up my new shoes, they're leather. Let's just hail a cab."

Throwing their trash away and walking towards the bustling streets, they easily found a cab they could take. Taxi's were in abundance in New York, so it wasn't an issue of finding one, it was more of a problem actually being able to get anywhere in it, what with the horrible traffic.

Shuffling into the backseat, Kendall giving the driver the directions of his apartment, the two settled into the plush interior. The cab was pitch dark, the only source of light being the glare of the radio screen and the Manhattan lights shining through the tinted windows. A soft cyan glow faintly illuminated the backseat, enough so for them to see the lazy grins on one another's face.

They barely talked, the two enjoying the colors of the in-motion vehicles driving by and the various sites to see, tourists all over taking pictures of the destination spot.

That was fine, though, the company of one another being more than enough to end the night on a good note. Being so close to one another was nice, their shoulders pressed against one another and thighs almost touching.

For Kendall, as weird as it was, it was almost as though he could feel his heartbeat electric to his fingertips, feeling a weird sensation of jitters as he sat next to the older business man, chalking it up to the high of the night, a genuinely good time spent between one another. Besides Logan and his bandmates, he hadn't really hung out with too many people, mostly due to being so busy all the time. Dinner was a cool break from it all.

For James, on the other hand, he could feel the anticipation through his veins as thought about his next step he would make as he tried to bed Kendall. Tonight had gone without a hitch, he had Kendall wrapped around his little finger. As he sat closer, throwing his arm around the back of the seat casually, he knew that Kendall would practically be begging James to fuck him any second now.

The ride carried on, and while it seemed as though they were catching every red light, neither really cared, glad that it just meant more time to spend with some one they could get close to.

Their legs were tangled up in the small space, but neither Kendall nor James tried to inch away from the other guy, especially since there was hardly any room for them to do so.

It stayed like this for the next 15 minutes, neither saying a word as they took it all in, finding themselves entering the residential area.

"Hey, we're already here, I can see my apartment complex up ahead, so I can just get out right now." Kendall said to the driver, handing him his cab fare as he opened the door and crawled out of the vehicle. Propping his forearms against the hood of the car, he beckoned towards the brunet. "Listen, thanks again for tonight, James. It was cool getting to hang out with someone I can call an actual friend, let's not make this the last. Heh, if I had it my way, we would have just stayed up all night."

With that, he walked away, heavy rain hitting him as he made his way to the door of the Brownstone, giving one last wave as he disappeared out of sight.

James had considered testing his luck with the blonde, inviting himself in and then pounding him senseless on his own bed. Anything could have happened on a night like this, but he knew it would be better to play it cool and strike when he knew it was the perfect time.

Baby steps, James. Baby steps.

* * *

 _ **Author's Note:** Thanks so much guys for all of the reviews on the previous chapters! I truly hope you're all enjoying the story, not too much longer until it's all wrapped up. ^_^_


	5. Superstar

**_~ One Week Later ~_**

 ** _Saturday Evening, 11:48 PM_**

* * *

"Yeah, I'm in the area, I know that for sure. Make a left? Your left or mine… oh, nevermind. I see it. Okay, pulling up now, your ass better be ready."

With a tap of his touch screen, he ended the call and placed his phone in one of the nearby compartments in the interior of his car. Easing his foot on the brake pedal, slowing down his car as he tried to find a spot to temporarily park his black Audi A6, a brand new 2015 model (of course), he saw an available space not too far from Kendall's brownstone. Putting the vehicle in park, he quickly got out, looking both ways as he made his way over to the somewhat familiar building, this barely being the second time he had been to the place Kendall called home.

Tonight was boy's night, the event having been planned out earlier on in the week. James and Kendall had grabbed lunch together a couple of times during the work week, most of the time hitting up the familiar burger joint they had first gone to. And, by James's request, the two had also gone to Chez Fancee, a favorite of the business man. Kendall was impressed, even if he didn't understand what a single word on the menu meant, just ordering whatever it was that James had. A dimpled smile later revealed that he still preferred the greasy burgers from before, though.

James had footed every single bill, which was later met with minor annoyance by Kendall. He had felt bad that James was paying for everything, especially with how expensive it surprisingly was for just two guys. James waved it off, telling Kendall that he could pick up the next tab if he had wanted to, which Kendall happily agreed to.

That was a lie, though. James threw his money at the waiter before Kendall could even dig his wallet from out of his pockets, which was met with a scowl from Kendall afterwards. His bank account was taking a heavy hit, but he could overlook that, even if the dollar amount was quickly dwindling.

Over lunch, they had decided that they had wanted to actually do something a bit more fun than just eating onion rings. Well, James had mostly decided, since Kendall was perfectly content just shoving fried food in his face. Kendall had agreed, though, a mouthful of carbs allowing for a barely understandable " _Sure, sounds fun"._

Wanting to form a bit of a friend group between the two men, Kendall would invite his friend Logan to go out with them, who he had told James all about, despite the brunet knowing quite a bit about him from their earlier webcam show. James, on the other hand, would bring along a non-existent friend named _Bart_ , who would " _unfortunately_ " be unable to tag along, leaving poor James to have to spend the night with _two_ hot guys. A tragedy, really.

Logan ended up cancelling at the last minute, however, as he would be on-call for his internship at the hospital the following day. Not too much of an issue for James, though, he had mainly just wanted to hang out with the blonde. Logan was just a potential side bonus.

Apart from that, he had a good feeling about tonight, if he would be able to pull all the tricks from out his sleeve (as James Diamond was always successfully able to do), there was no doubt that he'd be slamming Kendall's body into his mattress for all of the neighbors to hear.

Wanting to impress the blonde, he had made sure to look his best, wearing a black leather jacket paired with a cream colored shirt and dark form-fitting jeans that accentuated his form. He had an excellent sense of style, something he was unfortunately unable to show off all that often when his wardrobe primarily consisted of business suits. Not to say he didn't look handsome in those either, though.

It could have all been in vain, seeing as how Kendall's work outfits were usually so ill-matched and improperly ironed. And considering he usually only wore a backwards baseball hat and shorts when he was webcamming, James's wasn't too sure how much Kendall even cared about fashion, probably not even batting an eye at James's pricey clothing.

If Kendall could care less about what James was wearing, then whatever. He'd definitely enjoy what the brunet **_wouldn't_** be wearing later tonight.

Rapping his knuckles against the wooden door of the apartment complex, hand propped up against the doorframe as he awaited a response, he heard a pair of footsteps sounding as the figure got closer and closer, door swinging open as he was face to face with a certain genius.

" _Uhhh_ , can I help you?" Logan asked, nervously licking his lips as the taller male just smirked at him, peering down as he made intense eye contact, scaring the poor kid shitless.

"In more ways than one, handsome. But right now I'm looking for your friend, Kendall? Any chance he may be around?" James replied, grinning as he saw the smaller male swallow.

"Um… yes. I'll go get him. Just… stay there."

As Logan closed the door behind him, James could hear the faint voices of the two roommates.

* * *

" _Oh my god, Kendall, get down here! Your date's here and I didn't expect_ ** _him_** _to be the type of guy you hang out with!"_

" _Coming, coming. Not a date, and what's wrong with_ ** _him_** _? You make it sound like he's a creep or something."_

" _It's him!_ ** _Him_** _! James Diamond! Holy shit Kendall, how did you even meet the guy?"_

" _James? Uh, we work together? I'm pretty sure I mentioned that. How do you even know who he is though?"_

" _Because I don't live under a rock? He's like, super rich, dude. I have a couple of stocks invested in his company. "_ ** _We work together_** _", ha, you made it sound like you were hanging out with James the vending machine operator, not James the millionaire."_

" _Who cares? He's a chill guy, he's no way different from you and me, we're just gonna get a couple of drinks, nothing special. Sounds like you're a little jealous, Logie."_

 _"What? **No I'm not** , look, how many times do I have to tell you Kendall? I li-"_

 _"You like girls, I got it. I'm just pulling your leg, man. But don't worry, tonight's not_ _a big deal. And don't wait up for me, you gotta get up early tomorrow. Later man."_

" _Yeah, later bro..."_

* * *

Quickly throwing the door open, Kendall was standing in front of James, a dimpled smile greeting the older male. James had to say, the kid could surprisingly clean up well. Watching as he flattened down the fabric of his shirt, a grey button up with the sleeves rolled to his elbows, black skinny jeans, and what appeared as though the blonde had actually taken a brush to his hair, the sandy colored tresses neatly spiked and styled.

"I know, I know. I look hot. But what are you waiting for, lead the way!" Kendall beamed, James raising an eyebrow as he led him over to his parked Audi. Looking both ways, a steady flow of traffic easing up allowing the two to cross over, James quickly unlocked the doors, both men shuffling inside. "Oh yeah, nice to see you again, of course. Sorry I took so long, had to find something decent enough to wear for our big boy's night." he said, looking over at the older male who sent him a spine-chilling smolder. "Nice car, by the way." Kendall said, adjusting his seat to a comfortable recline. "Maybe we can just chill in here for the night, heh."

He'd be lying if he said he hadn't considered the idea, throwing Kendall in the back seat as he pounded into him, windows fogging up from the heavy breathing and low grunts echoing within the confined space. It was a good plan, despite how unlikely it may have been. It would have to be put on the backburner for the time being.

"As tempting as that sounds, I was thinking we'd do something a bit better. Even though the whole " _Boy's Night_ " thing kinda crashed and burn, I didn't want that to stop the two of us from enjoying ourselves. Thought we'd hit up the Palm Woods, real nice club not too far from here, just opened up not too long ago." James said, putting the his car in gear as he pulled out of the tight parallel parking space, finally able to bring his car to a steady glide down the streets of New York.

"Haven't heard of it. Granted, the only place I ever go to for cheap drinks is this nearby bar, so tonight will be a nice change from the usual. But don't these places have, like, guest lists or something? Or a cover charge?" Kendall asked, looking around the interior of the car, checking out the little gadgets and features his old Ford truck definitely didn't have.

"Ha, don't sweat it, I've got that all under control."

* * *

Walking down the sidewalk, hands in their pockets as the cold night air of the city nipped at their skin, they eventually found themselves standing in front of The Palm Woods, an upscale nightclub with a Southern California influence. A long line had formed outside the doors, clubgoers hoping to be granted access and not have the night end in such a lackluster way.

"Shit, look at the line. Should we just wait?" Kendall said, craning his neck as he saw the massive crowd of people stretched around the corner of the building.

"Ha, yeah right. Come on, follow me. Don't say anything, just… look pretty."

Strutting towards the entrance, James flashed the bouncer a charismatic smile, his mannerisms cool and collected and sure to persuade anybody. "VIP. James Diamond, brought a guest with me."

Looking him up and down, the bald security guard tried to determine who exactly the two men were. Pulling out his clipboard, he ran his finger along the page, trying to see if what he said was true.

"Let me see… James Diamond, _Diamond_ , _Diamond_. Oh, yeah, you're on the list bro. Pretty exclusive tonight though, who's the friend?"

Before he could speak up, the beginning of a sentence already on the tip of the blonde's tongue, James immediately cut off Kendall. " _Dak Zevon_. I'm assuming you've heard of him?"

"Yeah, I have." Lifting up the velvet rope, he looked over his shoulder and yelled out a " _they're good_ ", motioning the two men inside. "Enjoy your night fellas."

Muttering a thanks, the duo walked through the opening of the building, immediately seeing the mass of bodies gyrating amongst one another along the interior of the club. The dance floor was packed, as was the bar, young and attractive bartenders quickly serving up drinks without a blink of the eye, a guest DJ performing whom Kendall had heard of, and sparks and confetti being shot across the room. As stupid as it was, Kendall had always assumed these types of events were only in movies and scripted reality tv programs. The fact that he was actually experiencing it firsthand was surreal.

"Anything like you were hoping it'd be?" James leaned in, whispering into Kendall's ear, barely audible over the loud rhythm of the music, the vibrations of the sound waves able to be felt in your bones.

"Yeah man, this place is sick. Thanks for bringing me." Kendall replied, earning a curt nod from the older male.

"Yeah, well, we barely just got here. Wait till we actually get to the fun stuff. Like getting you shitfaced."

Kendall laughed, mouthing an "okay" as he and James walked over to the open bar. Squeezing their way in, hot sweaty bodies rubbing against them, they had managed to make it to the front of the bar. The bartenders immediately took notice of them, stopping what they were doing to serve them.

Something about James Diamond just seemed to catch everybody's interest. As everyone catered to the business man, Kendall noticed it. He was in his element, shining bright like a star with people wanting to be wherever he was. It was as though he could take over the entire club if he had possibly wanted to.

Perhaps Logan was right, maybe his name did hold some weight. He was certainly good looking too, his suave personality, mannerisms, and overall sense of star power apparently easy to recognize in a sea of faces. For others, being in the presence of James Diamond, let alone _hanging out_ with the guy, would be beyond intimidating.

Yet Kendall didn't feel that way. To him, James was just another guy he could talk to. A friend.

"Blondie, whatcha want to drink? My treat, man." James said, reading the short menu listing all of the various alcoholic beverages the place had to offer.

"Uh, I don't know, a beer?" Kendall replied, earning a condescending smirk and a raised eyebrow from the business man. "What, not wild enough for you? Shit, get me a whiskey then, haha."

"Awesome, now come on and take a seat." James responded, pulling out a brightly colored stool for the blonde to sit on. "Waiter! Yeah, we'll take a whiskey on the rocks, uh huh, and a Pina Colada, hold the liquor." He couldn't drink tonight, especially if he was driving.

"Coming right up!"

"Awesome." James said, turning his body towards the dance floor and taking in the atmosphere. "So? What's next on the agenda?"

"Well, assuming you don't want Boy's Night to flop, the only obvious choice would be to dance after this. Can't wait to show you my moves, I've been practicing all week." Kendall grinned, earning a light chuckle from the older male.

"That so? Can't wait to see, then."

The two got their drinks immediately after, both toasting to the night and taking quick gulps of their drinks. James's drink was easy going down, especially since it was non-alcoholic. Kendall winced as he took a chug of his, slamming the glass down on the counter with a look of pride.

"Ha, that was nothing. Get me another one stat."

"That wasn't a shot you know, like, you could have tried to savor it, but fuck, okay I guess." James replied, Kendall rolling his eyes as he laughed at his remark.

"What, I like to let loose every once in a while. It's hard when you have to juggle work and school, sue me."

* * *

After another glass of whiskey and two and a half shots of tequila (the third shot mostly ending up on his shirt), Kendall was feeling a little buzzed. He had decided to quit it there, not wanting to get completely hammered twenty minutes into the night. Kendall could actually hold his liquor, much to James's surprise. It was a good thing, though. At least Kendall would have a recollection of the night's events the next morning.

As he leaned back against the bar counter, Kendall was in awe, eyes searching all over the club as James pointed out the various celebrities and socialites, noting who was cool, who wasn't, who was an asshole, amongst other labels. Kendall wasn't the type to be star struck, a firm believer that the people who popped up on the tabloids were just like him. But being around all these stars gave him hope, hope that one day he would be discovered and he'd be one of the familiar faces in the crowd. Hope that Kendall Knight would someday be as admired as James Diamond was.

After Kendall's little drinking binge, they made their way over to the dance floor, both dancing considerably close to one another due to the large amount of people surrounding them. Expectedly, James was a great dancer, the way he moved his hips hypnotizing to Kendall and probably everyone within a 5 mile radius of the business man. Kendall, on the other hand, was a little off beat, the reason either being because he was tipsy or because he had a lack of internal rhythm. Either way, he was having fun, him and James laughing the entire time as they just let loose.

James decided to step things up a notch, inching closer and closer to the blonde, placing his hands on the younger guy's hips, Kendall immediately taking notice, laughing as he bit his lip.

"Woah, _hellooo James_ …" Kendall drawled out, putting his hands on top of James's, guiding them lower and lower until they were firmly groping his ass. He began to grind against James, chests bumping against one another, crotches rubbing together. Each guy was getting hard, evident to the both of them, heated stares as the moment just grew more and more intimate.

"Holy shit Kendall, you don't know how much I wanted this. Fuck, won't your boyfriend be jealous?" James mocked, smirking as a puzzled look flashed across Kendall's face.

"Boyfriend? Who, _Logan_? Ha, are you kidding me, he's _still_ pretending that he's straight." Kendall said, snorting at James's remark. "Nah, forget Logan, let's just focus on us. Here. Let me show you."

Taking James by surprise, Kendall smashed their lips together, his hands cupping the sides of James's face as the older male gripped the blonde's ass even tighter, hands rubbing all along his lower back. Tongues were pressed, saliva was mixed, lips disconnecting every once in a while as they tried to catch their breaths.

"Let's take this somewhere else, babe. Where we don't have an audience." James said, Kendall slowly nodding his head as he felt intoxicated from the kiss, if that were even possible.

Deciding to get just a slight more privacy then this, they continued over in the lounge area, James being a VIP after all. It was remarkably less packed, seating areas separated by see-through curtains, allowing for smaller parties to actually have their own personal space.

It was a bit awkward at first, for Kendall at least. They had just gone from dry-humping and swapping spit smack dab in the middle of probably 200 people, and now they were seated next to each other, James's arm resting against the back of his neck. At this point, Kendall was mentally screaming as each second passed where James hadn't just pounced him, sinking his teeth into his skin as he told him all the dirty things he wanted to do to him. He had gone from confident Kendall who had made the first move to nervous Kendall who wasn't quite sure where to go from here. For all he knew, James could have brought him over here just to beat the shit out of him for being gay.

"Heh, _sooo_ … that was pretty fun." Kendall said, gulping as he turned his head and saw James's hand kneading his right bicep. Kendall looked down, airing out the collar of his shirt as he could feel himself sweating. The two sat in silence for what was probably only a few seconds, yet it felt as though it was much longer than that. They took in the atmosphere, Kendall noting that he could faintly hear " _Like A G6_ " blasting throughout the building.

"Oh, I like this song, takes me back to 2010…" Kendall said, stating the obvious. James only slowly nodded, obviously not interested in making pointless small talk like this. "Haha, _okay_ …so what do you wanna do next, James _?"_

"Hmm, I'm not sure. We already drank, we already danced, it's up to you man. _Surprise me_ , I'm up for **_anything_**." James said, husky voice as he just smiled at Kendall, a look of lust that just sent a surge of confidence throughout the blonde's body that he had absolutely needed.

Like a flash of lightning, he jumped on top of James, straddling his lap as he desperately continued where he had left off with James, a sense of eagerness and need shared between the two. Perhaps it was just the alcohol, but Kendall was feeling like a rabid animal at this point, blindly kissing the older male, occasionally missing the mark and pressing his lips all over his face. It was sloppy and put a literal definition to " _sucking face_ ", but neither guy hardly cared. He could feel James's fingers digging into his ass, a hand slipping into the back of his jeans, cupping his bare cheek.

They stayed in this position for a while, Kendall grinding his ass down on top of James's rock hard erection, his own rubbing against the front of the brunet's stomach. Shifting, James pushed Kendall back against the white leather seating, hovering over him as he pinned his hands back behind his head, exerting his dominance over the guy who seemed to have no problem playing the submissive role. James pulled the curtain back a bit, preventing anybody from watching the two all but getting it on.

It was everything James had wanted, the harsh purple lighting framing the blonde's facial structure perfectly, sharp jawline accentuated and coarse facial hair contrasting against the neon lights. A light sheen of sweat was painted over Kendall's skin, the blonde huffing and puffing from the hot and heavy moment.

It only made James want to continue that much more.

And he did. Wet sounds and low growls were made, both guys practically near orgasm at this point. As their bodies became tangled, Kendall accidentally kicked over a bottle of Vodka resting on the table service cart, not paying attention to the loud crash it made as it hit the dark wood flooring. He was focused on crashing his lips against James's instead.

As they continued to make out, hands rubbing all over, soft moans escaping from parted lips, James could feel Kendall's hand pressing against his crotch, massaging the outline of his length.

If his eyes hadn't been closed, James was sure they would have rolled impossibly far into the back of his skull. He continued to kiss the blonde, biting down on his lower lip that caused Kendall to let out a guttural moan. He moved his lips over to the blonde's neck, sucking hard which would surely leave a noticeable hickey.

Caught up in the moment, Kendall eased his wrists out of James's tight grasp, using his fingers to deftly tug at the business man's belt buckle, loosening it up just enough to be able to stick a hand in and wrap a fist around James's dick, slick with precum. James almost head butted the white marble wall in front of him, the satisfaction the blonde was giving him causing his body to unexpectedly jerk forward. He knew Kendall was kinky, but he was surprised that he would get so carried away in a public setting like this.

In that moment, he realized just how obvious they were being behind the closed curtain. As he heard the light sounds of voices and music in the background, James snapped out of reality and realized that he and Kendall were just about to have sex inside a packed club with people surrounding them.

" _Fuck_ , not that I don't want this Kendall, but not here. Come on, let's head out." James grunted, sentence disconnected as he could feel Kendall thumbing over the sensitive head, somehow knowing everything that just made James tick.

Fixing his clothes and hair, hiding the fact that he had just had a hot and heavy moment with Kendall, he needed to get out of here as soon as possible. Grabbing the blonde's hand, he led him to the exit of the club and back to his car, not wanting to lose Kendall in the large crowd. They eventually made their way outside, the sudden drop in temperature sending chills down their spines, but they hardly paid any attention to it. James hit the unlock button on his car keys, a loud beep signaling where it was that they had parked.

They immediately took off, James driving back over to Kendall's place. It was dead silent, an air of sexual tension evident between the two. He was only a few streets away when he felt a tugging at the zipper of his jeans. Looking down, he saw Kendall inching closer and closer to his lap.

"Kendall! Not now, fuck, you want me to get in a crash?"

"What can I say, I'm a _freak_."

With that, James all but flew down the streets, the roads relatively empty, especially since it was two in the morning. Seeing Kendall's apartment in view, he maneuvered his car into the same parking space as before, putting the vehicle in park and swiftly reclining the seat. It had only taken a few minutes for James to put the car in park, but for Kendall, it felt like hours.

Lunging over at the brunet, clawing at his jeans as he tried to at least get the fabric down to the middle of his thighs, he maneuvered the older male's dick out of the slit of his boxers, spitting into his hand as he began to pump him until he was fully erect again.

"Oh shit, just like that Kendall, fuck it feels so good. Wanna feel those lips, dammit." James moaned, looking over at Kendall who seemed to be more than eager to do so.

Leaning over, he took James's cock into his mouth, lightly lapping around the head as he savored the taste. Dragging his tongue along the underside of his length, keeping eye contact with the older male the entire time in the almost pitch black interior of the car, only source of lighting being a nearby street lamp, he knew he was doing something right judging by how crazy he was driving the brunet.

"Oh fuck Kendall, _just like that_ , fucking take it and gag on it."

"You like it, huh? I love it, love how fucking _big_ you are, fuck James, I didn't know you were packing heat." Kendall said, the end of his sentence broken as popped on and off of James's cock, saliva running down the sides of his short beard. "God, wish you could fuck me all night long, baby. Fuck me raw until I'm screaming for more. Biggest cock I've ever seen in my fucking life."

The dirty talk was really getting to James, the same dirty talk he had heard the blonde use on his webcam show. Kendall could use that mouth of his in many ways, each way sending jolts of pleasure throughout his body. Thrusting his hips into Kendall's mouth, the younger male gagging and choking a bit, he had his hand on the back of his head, pulling the sandy locks as his guided him up and down.

"Fuck, I bet your friend is watching us from his window, jacking himself off, probably seeing how much of a whore you are, huh?" James moaned, Kendall snorting a bit at the remark, mentally laughing because he wouldn't put it past the genius to do something like that.

It had happened before.

He continued to suck him off, slapping James's dick against the base of his tongue. He would alternate between sucking and licking, cheeks hollowed as he would continue to bob his head up and down. He could feel his dick painfully rubbing against the tight fabric of his jeans, but he didn't care, he was too focused on pleasuring James.

"Oh god, keep doing that and I'm gonna cum any second. Fuck, this is the best fucking head I've ever gotten. Work that mouth, just like that." James groaned, hand clutching the arm rest of the driver's side door, other hand practically ripping every hair out of the blonde's head. Kendall didn't seem to mind, though, as he was currently humming along to some beat as he satisfied the older male, a bit of cockiness and experience to his actions.

He knew he'd be cumming soon, not lasting as long as he usually would, no doubt because of the blonde's finesse. He rapidly began to move his hips up and down, face fucking Kendall at this point. "Oh god Kendall, I'm gonna cum, _oh shit_ …"

Forcefully holding the blonde's head down, Kendall choking as he deep throated all of James, air wave access limited, the older male let it out, ropes of cum shooting into the back of Kendall's throat. Kendall really was a pro, managing to take it all hold for the few drops that leaked out onto James's boxers and the hairs of his exposed thighs.

Pulling off, he immediately met James for a kiss, swapping the load between their mouths, much to James's unexpected delight. It was so erotic, tasting himself mixed with Kendall's spit, the taste of whiskey evident as they carried on their make out session from earlier. Swallowing his cum down, strings connecting their lips, neither wanted this to end anytime soon.

"Fuck, that was so hot Kendall. Now come on, lean back and let me show you what **_I_** can do." James moaned, still trying to regain his breath.

"Shit, as much as I'd love to, I really gotta go. It's already 2:25, I've gotta get up early tomorrow." Kendall responded, running a hand through his hair, getting himself situated as he climbed out of the car.

"Dude, really? Come on, I feel bad now, especially since you've still got _that_ going on." James replied, pointing at the very noticeable tent in the blonde's jeans. "Let me return the favor."

"It's cool man, really, I'll just go and rub one out in the shower. Lord knows I have some new material to work with." Kendall said, smirking as he closed the car door in front of him. "Don't be a stranger, I had a lot of fun tonight. Let's do this again, and hey, maybe next time I'll use _more_ than just my mouth."

"Fuck, definitely. Night, Kendall."

Smiling, Kendall waved goodbye, doing a light jog as he made his way over to his apartment. James stayed there for a few minutes, watching as the soft glow emitting from the living room window quickly faded back to black, no doubt Kendall finally showering and then going to bed.

Pulling his vehicle out, he made his way back over to his own loft. Tonight was great, it was everything he had wanted.

But he still needed more.

* * *

 _ **Author's Note:** Sorry this took so long guys, I had some trouble decided how to go about this chapter. I was listening to Big Time Rush's very iconic chart topping smash hit "Superstar" when it gave me some inspiration about what to write. So yeah, hope you enjoy it! Almost at the end, too. :-0_


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